WO2020199996A1 - Composé de 1,3,5-triazine substitué, composition et utilisation associées - Google Patents

Composé de 1,3,5-triazine substitué, composition et utilisation associées Download PDF

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WO2020199996A1
WO2020199996A1 PCT/CN2020/081035 CN2020081035W WO2020199996A1 WO 2020199996 A1 WO2020199996 A1 WO 2020199996A1 CN 2020081035 W CN2020081035 W CN 2020081035W WO 2020199996 A1 WO2020199996 A1 WO 2020199996A1
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independently
compound
substituted
alkyl group
element content
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王悦
李成龙
张佐伦
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吉林省元合电子材料有限公司
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Priority to KR1020217035151A priority Critical patent/KR102663374B1/ko
Priority to JP2021560344A priority patent/JP7236772B2/ja
Publication of WO2020199996A1 publication Critical patent/WO2020199996A1/fr

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Definitions

  • the invention relates to a substituted 1,3,5-triazine compound, composition and application thereof.
  • Pope et al. first reported the phenomenon of organic electroluminescence. They observed the blue light emitted by anthracene when a high voltage of 400 volts was applied on both sides of an anthracene single crystal (see M. Pope, H. Kallmann and P. Magnante, J. Chem. Phys., 1963, 38, 2042). However, because single crystals are difficult to grow and the device drive voltage is high, the processes they use have almost no practical use. Until 1987, CWTang et al.
  • the device obtains green light emission with a brightness of up to 1000 cd/m 2 under a driving voltage of 10V, and the device efficiency is 1.5 lm/W (see CWTang and SAVan Slyke, Appl. Phys. Lett., 1987, 51, 913). This breakthrough has enabled organic electroluminescence research to be carried out rapidly and deeply in the world.
  • phosphorescent materials generally use precious metals such as iridium and platinum, which are expensive.
  • precious metals such as iridium and platinum
  • they still have chemical instability, and the device has problems such as large efficiency roll-off under high current density.
  • An OLED device that uses cheap and stable organic small molecule materials and can achieve high-efficiency light emission is extremely important.
  • organic electroluminescence technology has received extensive research and attention in the scientific and industrial circles.
  • Organic small molecule optoelectronic materials are widely used as high-performance materials because of their clear structure, easy modification, simple purification and processing.
  • traditional fluorescent dye molecules often have very high fluorescence quantum yields, but their doped OLED devices are limited by the internal quantum efficiency of 25%, and the external quantum efficiency is generally lower than 5%, which is lower than the efficiency of phosphorescent devices.
  • red dye DCM see CWTang, SAVan Slyke, and CH Chen, J. Appl.
  • fluorescent OLED devices that can break through the 25% internal quantum efficiency limit mainly adopt a delayed fluorescence mechanism, which can effectively utilize the triplet excited state energy in the device.
  • TTA Triplet-Triplet Annihilation, triplet-triple annihilation
  • TADF Thermally Activated Delayed Fluorescence
  • the TTA mechanism is a mechanism that uses the fusion of two triplet excitons to generate singlet excitons to increase the generation rate of singlet excitons, but the maximum internal quantum efficiency of the device is only 40% to 62.5%.
  • the TADF mechanism uses organic small molecular materials with a small singlet-triplet energy level difference ( ⁇ EST).
  • the triplet excitons can be converted into singlet through the reverse intersystem crossing (RISC) process under ambient thermal energy.
  • RISC reverse intersystem crossing
  • the mechanism of heavy state excitons In theory, the quantum efficiency of the device can reach 100%.
  • TADF molecules are mainly used as guest materials doped in wide-bandgap host materials to achieve high-efficiency thermally activated delayed fluorescence (see Q. Zhang, J. Li, K. Shizu, S.
  • TADF material Because it can simultaneously use singlet and triplet excitons to emit light, the performance of the electroluminescent device of TADF material is significantly improved compared with traditional fluorescent devices. In addition, compared with traditional phosphorescent materials, TADF materials are inexpensive, which is more conducive to their commercial promotion and application. At present, TADF molecules of various light colors have been synthesized from deep blue to near-infrared light emission, and the performance of some devices is comparable to traditional phosphorescent devices. Traditional single-molecule TADF materials generally consist of donor (D) and acceptor (A) units.
  • Exciplex luminescence is a charge transfer excited state luminescence behavior between a donor molecule and an acceptor molecule. Its luminescence comes from the electrons between the LUMO orbital of the acceptor molecule and the HOMO orbital of the donor molecule. Jump. Since the HOMO and LUMO orbitals of the exciplex are concentrated on the donor and acceptor molecules, the corresponding singlet and triplet energy level differences tend to be smaller compared with single-molecule TADF materials.
  • exciplexes can also achieve efficient thermally activated delayed fluorescence emission.
  • Donor molecules and acceptor molecules can not only form exciplexes as a light-emitting layer to emit light, but also serve as hole transport and electron transport layers, respectively, which simplifies the structure of the device to a certain extent.
  • the molecular interface between the donor and acceptor can also produce exciplex luminescence similar to the planar heterojunction (PN) (see: Advanced Materials, 2016, 28 , 239-244).
  • PN planar heterojunction
  • Electroluminescent devices prepared with excimer complexes as co-hosts have many advantages such as low turn-on, high efficiency, and low roll-off, and have become a hot topic in current research (see: Advanced Functional Materials, 2015, 25, 361-366).
  • CN108218836A discloses two tris (phenyl/pyridine-benzimidazole) benzene/pyridine compounds (E1 and E2) as shown below. These two compounds can be used as electron acceptors and electron donors to construct a light-emitting layer. Similar materials can also be used as electron transport in electroluminescent devices.
  • E1 or E2 is used as an electron acceptor and an electron donor to construct a light-emitting layer, while E1 or E2 is used as an electron transport material, the efficiency of the prepared light-emitting device is low, and the stability of the device is poor.
  • the molecule as an electron acceptor material can be combined with some electron donor materials as the host material of the electroluminescence device, and the material can also be used as an electron transport layer for the electroluminescence device at the same time.
  • CN106946859A discloses a series of triazine compounds substituted with bisbenzimidazole and its derivatives, and points out that these compounds can be used as hole blocking layers and electron transport layers in electroluminescent devices, and these compounds can be used as light extraction layers or electron transport layers.
  • the layer is used in electroluminescent devices, which can improve the efficiency of the device to a certain extent.
  • CBP 4,4'-dicarbazole biphenyl
  • CN102593374B discloses the following three compounds (TPT-07, TBT-07 and TBT-14) as the electron transport layer and host material for the preparation of electroluminescent devices. However, the efficiency of the prepared light-emitting device is low.
  • the problem to be solved by the present invention is the deficiency of existing electron acceptor materials and electron transport materials, and provides a 1,3,5-triazine compound, composition and application thereof.
  • the 1,3,5-triazine compound of the present invention can not only be used as an electron transport material for preparing the electron transport layer of an electroluminescent device, but also can be used as an electron acceptor material, and a combination of it and an electron donor material can be used as The host material of the electroluminescent device, the electroluminescent device prepared therefrom has the advantages of higher efficiency and longer life; furthermore, the 1,3,5-triazine compound is used as the electron transport layer at the same time as The combination of the electron acceptor material and the electron donor material constructs a light-emitting layer, and the prepared electroluminescent device has the advantages of better high efficiency, longer life and the like.
  • the present invention solves the above technical problems through the following technical solutions.
  • the present invention provides a 1,3,5-triazine compound as shown in formula I,
  • R 1 , R 2 , R 3 , R 4 and R 5 are independently R; the rest (ie, R 1 , R 2 , R 3 , R 4 and R 5 are not R
  • R 1 , R 2 , R 3 , R 4 and R 5 are independently R
  • R 3 is independently R
  • R 1 , R 2 , R 4 and R 5 Is not R
  • R 2 and R 4 are independently R, R 1 , R 3 and R 5 Not R
  • R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently hydrogen, deuterium, halogen, cyano, C 1 ⁇ C 10 alkane group, with one or more substituents R a-1 is C 1 ⁇ C 10 alkyl group, C 1 ⁇ C 10 alkyl group -O-, with one or more R a-2 substituted C 1 ⁇ C 10 alkyl group -O-, C 6 ⁇ C 14 aryl group, substituted with one or more R a-3 substituted C 6 ⁇ C 14 aryl, 5-6 membered monocyclic heteroaryl, substituted with one or more R a-4 Substituted 5-6 membered monocyclic heteroaryl or The heteroatoms in the 5-6 membered monocyclic heteroaryl group and the 5-6 membered monocyclic heteroaryl group substituted by one or more Ra -4 The definition is as follows: the hetero
  • R is independently
  • n1 and n2 are independently 1, 2, 3 or 4; n3 is 1, 2 or 3;
  • R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 , R 2-3 are independently hydrogen, deuterium, halogen, cyano, C 1 ⁇ C 10 alkyl group, C 1 ⁇ C 10 alkyl group substituted by one or more R b-1 , C 1 ⁇ C 10 alkyl group-O-, C 1 ⁇ C 10 substituted by one or more R b-2 alkyl -O-, C 6 ⁇ C 14 aryl group, substituted with one or more R b-3 is unsubstituted C 6 ⁇ C 14 aryl, 5-6 membered monocyclic heteroaryl, substituted with one or more R b -4 substituted 5-6 membered monocyclic heteroaryl or The heteroatoms in the 5-6 membered monocyclic heteroaryl group and the 5-6 membered monocyclic heteroaryl group substituted by one or more R b-4 The definition is as follows: heteroatoms are selected from one or more of N,
  • heteroatom is N, and the number of heteroatoms is 1 to 3; when R c-1 and R c-2 are independently multiple, they are the same or different;
  • R a-1 , R a-2 , R a-3 , R a-4 , R b-1 , R b-2 , R b-3 , R b-4 , R c-1 and R c-2 are independent Ground is the following substituents: deuterium, halogen, cyano, trifluoromethyl, C 1 -C 6 alkyl or C 1 -C 6 alkyl-O-.
  • the definitions of certain substituents in the 1,3,5-triazine compound represented by formula I can be as follows, and the definitions of unmentioned substituents are as described in any of the above schemes .
  • R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 , R 2-3 , R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently halogens, and the halogens (such as fluorine, chlorine, bromine or iodine) are independently fluorine.
  • R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently C 1 to C 10 alkyl, substituted with one or more substituents
  • R a-1 is C 1 ⁇ C 10 alkyl group, C 1 ⁇ C 10 alkyl group by one or more -O- R a-2 substituted by C 1 ⁇ C 10 alkyl
  • the C 1 ⁇ C 10 alkyl group is independently a C 1 ⁇ C 6 alkyl group (for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, butyl, isobutyl, pentyl or hexyl group), preferably a C 1 ⁇ C 4 alkyl group (e.g. methyl, ethyl, n-propyl, iso
  • R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently C 6 ⁇ C 14
  • the C 6 ⁇ C 14 aryl group is independently a C 6 ⁇ C 10 aryl group; for example, phenyl or naphthyl .
  • R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently 5-6 yuan unit
  • the C 1 ⁇ C 12 heteroaryl group is independently a heteroatom selected from N, the number of heteroatoms 1 to 3; preferably pyridyl.
  • R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 and R 2-3 are independently C 1 ⁇ C 10 alkyl group, C 1 ⁇ C 10 alkyl group substituted by one or more R b-1 , C 1 ⁇ C 10 alkyl group-O- or C 1 ⁇ C substituted by one or more R b-2
  • the C 1 ⁇ C 10 alkyl is independently C 1 ⁇ C 6 alkyl (for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl group, sec-butyl, isobutyl, pentyl or hexyl), preferably a C 1 ⁇ C 4 alkyl group (e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butoxy , I
  • R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 and R 2-3 are independently C 6 ⁇ In a C 14 aryl group or a C 6 ⁇ C 14 aryl group substituted by one or more R b-3 , the C 6 ⁇ C 14 aryl group is independently a C 6 ⁇ C 10 aryl group; for example, phenyl or Naphthyl.
  • R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 and R 2-3 are independently 5-6
  • the C 1 ⁇ C 12 heteroaryl group is independently a heteroatom selected from N, hetero The number of atoms is 1 to 3; preferably pyridyl.
  • said 5-6 membered monocyclic heteroaryl group is independently a 5-6 membered monocyclic heteroaryl group or a 5-6 membered monocyclic heteroaryl group substituted with one or more R c-2 , said 5-6 membered monocyclic heteroaryl group is independently
  • the heteroatom is selected from N, and the number of heteroatoms is 1 to 2; preferably, it is pyridyl.
  • R 6 and R 11 are the same, R 7 and R 12 are the same, R 8 and R 13 are the same, R 9 and R 14 are the same, and R 10 and R 15 are the same.
  • R is independently located on the benzene ring and The ortho, meta or para position of the connection site; preferably, when the number of R is 2, they are independently located on the benzene ring and The meta position of the connection site.
  • said halogen e.g. fluorine, chlorine, bromine or iodine
  • Ra -1 , Ra -2 , Ra -3 , Ra -4 , R b-1 , R b-2 , R b-3 , R b-4 , R c-1 and R c-2 are independently C 1 ⁇ C 6 alkyl or C 1 ⁇ C 6 alkyl-O-, the C 1 ⁇ C 6 alkyl or C 1 ⁇ C 6 alkyl
  • the C 1 ⁇ C 6 alkyl group in -O- for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, pentyl or hexyl
  • the ground is a C 1 -C 4 alkyl group (such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-buty
  • the number of R c-1 and R c-2 is 1, 2, or 3 independently.
  • R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently selected by one or more
  • a C 1 ⁇ C 10 alkyl group substituted by Ra-1 or a C 1 ⁇ C 10 alkyl group-O- substituted by one or more Ra -2 the substituted C 1 ⁇ C 10 alkyl group or substituted C 1 ⁇ C 10 alkyl group substituted with -O- in the C 1 ⁇ C 10 alkyl group is independently trifluoromethyl.
  • R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 and R 2-3 are independently Or more C 1 ⁇ C 10 alkyl substituted by R b-1 or C 1 ⁇ C 10 alkyl-O- substituted by one or more R b-2 , the substituted C 1 ⁇ C 10 alkyl or substituted C 1 ⁇ C 10 alkyl group substituted with -O- in the C 1 ⁇ C 10 alkyl group is independently trifluoromethyl.
  • R 1-1 , R 1-2 , R 1-3 and R 1-4 are independently hydrogen, deuterium, C 1 ⁇ C 10 alkyl group, and one or more R b-1 is substituted with C 1 ⁇ C 10 alkyl group, C 6 ⁇ C 14 aryl group, substituted with one or more R b-3 is unsubstituted C 6 ⁇ C 14 aryl, 5-6 membered monocyclic heteroaryl, 5-6 membered monocyclic heteroaryl substituted by one or more R b-4 or R 2-1 , R 2-2 and R 2-3 are independently hydrogen.
  • R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently hydrogen, deuterium, halogen , cyano, C 1 ⁇ C 10 alkyl group, with one or more substituents R a-1 is C 1 ⁇ C 10 alkyl group, C 6 ⁇ C 14 aryl group by one or more of the substituents R a-3 C 6 ⁇ C 14 aryl group; preferably hydrogen, deuterium, halo, cyano, C 1 ⁇ C 10 alkyl group by one or more substituents R a-1 is C 1 ⁇ C 10 alkyl group.
  • R is
  • R 1 , R 2 , R 3 , R 4 and R 5 are independently R; the rest are independently R Y1 ; R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14, and R 15 are independently hydrogen, deuterium, halogen, cyano, C 1 ⁇ C 10 alkyl, and one or more R a-1 a-substituted C 1 ⁇ C 10 alkyl group, C 6 ⁇ C 14 aryl group by one or more R a-3 substituted C 6 ⁇ C 14 aryl group;
  • R 6 and R 11 are the same, R 7 and R 12 are the same, R 8 and R 13 are the same, R 9 and R 14 are the same, and R 10 and R 15 are the same;
  • R is independently
  • R 1-1 , R 1-2 , R 1-3 and R 1-4 are independently hydrogen, deuterium, C 1 ⁇ C 10 alkyl, C 1 ⁇ C 10 substituted by one or more R b-1 alkyl group, C 6 ⁇ C 14 aryl group, substituted with one or more R b-3 is unsubstituted C 6 ⁇ C 14 aryl, 5-6 membered monocyclic heteroaryl, substituted with one or more R b-4 5-6 membered monocyclic heteroaryl group or R 2-1 , R 2-2 and R 2-3 are independently hydrogen.
  • R is the same.
  • one of R 1 , R 2 , R 3 , R 4 and R 5 is R; the rest are independently R Y1 ; or, R 2 and R 4 are independently R ; The rest are independently R Y1 ;
  • R 2 and R 4 are independently R, R 2 and R 4 are the same or different, for example the same.
  • R Y1 is independently hydrogen.
  • one of R 1 , R 2 , R 3 , R 4 and R 5 is R; the rest are independently R Y1 ; or, R 2 and R 4 are independently R ; The rest are independently R Y1 , and R Y1 are independently hydrogen.
  • R 8 and R 13 are independently hydrogen, halogen, C 1 ⁇ C 10 alkyl group, or by one or more substituents R a-1 is C 1 ⁇ C 10 alkyl group;
  • Ra -1 is independently halogen, such as fluorine
  • the C 1 -C 10 alkyl group substituted with one or more Ra -1 is trifluoromethyl.
  • R 6 , R 7 , R 9 , R 10 , R 11 , R 12 , R 14 and R 15 are independently hydrogen.
  • R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently hydrogen, halogen, C 1 ⁇ C 10 alkyl groups, or C 1 ⁇ C 10 alkyl groups substituted by one or more Ra -1 ;
  • R 8 and R 13 are independently hydrogen, halogen, C 1 ⁇ C 10 alkyl group, or by one or more substituents R a-1 is C 1 ⁇ C 10 alkyl group;
  • R 6, R 7, R 9 , R 10 , R 11 , R 12 , R 14 and R 15 are independently hydrogen;
  • R a-1 is independently halogen, such as fluorine; for another example, the C 1 to C 10 alkyl group substituted by one or more R a-1 is trifluoromethyl;
  • R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 , R 2-3 are independently hydrogen, C 6 ⁇ C 14 aryl group, substituted with one or more R b-3 is unsubstituted C 6 ⁇ C 14 aryl, 5-6 membered monocyclic heteroaryl, or
  • R 1-1, R 1-2, R 1-3, R 1-4 are independently hydrogen, C 6 ⁇ C 14 aryl group, substituted with one or more R b-3 is unsubstituted C 6 ⁇ C 14 Aryl, 5-6 membered monocyclic heteroaryl, or
  • R 2-1 , R 2-2 and R 2-3 are independently hydrogen.
  • R 1-1 , R 1-2 , R 1-3 , and R 1-4 are independently hydrogen, C 6 ⁇ C 14 aryl, and one or more R b- 3- substituted C 6 ⁇ C 14 aryl, 5-6 membered monocyclic heteroaryl, or
  • R b-3 is independently halogen, trifluoromethyl, or C 1 -C 6 alkyl.
  • R 2-1 , R 2-2 and R 2-3 are independently hydrogen.
  • one of R 1 , R 2 , R 3 , R 4 and R 5 is R; the rest are independently R Y1 ; or, R 2 and R 4 are independently R ; The rest are independently R Y1 , and R Y1 are independently hydrogen;
  • R is independently
  • R 2 and R 4 are independently R, R 2 and R 4 are the same or different;
  • R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently hydrogen, halogen, C 1 to C 10 alkyl, or one or more R a-1 is substituted with C 1 ⁇ C 10 alkyl group; R a-1 independently halogen;
  • R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 , R 2-3 are independently hydrogen, C 6 ⁇ C 14 aryl, and one or Multiple R b-3 substituted C 6 ⁇ C 14 aryl groups, 5-6 membered monocyclic heteroaryl groups, or R b-3 is independently halogen, trifluoromethyl or C 1 ⁇ C 6 alkyl;
  • R 2 and R 4 are independently R, R 2 and R 4 are the same;
  • R 8 and R 13 are independently hydrogen, halogen, C 1 ⁇ C 10 alkyl group, or by one or more substituents R a-1 is C 1 ⁇ C 10 alkyl group;
  • R a-1 is independently halogen
  • R 6 , R 7 , R 9 , R 10 , R 11 , R 12 , R 14 and R 15 are independently hydrogen;
  • R 1-1, R 1-2, R 1-3 , R 1-4 are independently hydrogen, C 6 ⁇ C 14 aryl group, substituted with one or more R b-3 is unsubstituted C 6 ⁇ C 14 aryl group , 5-6 membered monocyclic heteroaryl, or
  • R b-3 is independently halogen, trifluoromethyl or C 1 ⁇ C 6 alkyl
  • R 2-1 , R 2-2 and R 2-3 are independently hydrogen.
  • the 1,3,5-triazine compound represented by formula I is any one of the following compounds:
  • the compound of formula I of the present invention can be prepared according to conventional chemical synthesis methods in the art, and the steps and conditions can refer to the steps and conditions of similar reactions in the art.
  • the present invention provides a preparation method of 1,3,5-triazine compound as shown in formula I, which may include any of the following schemes:
  • R 1'and R 2' have the same definitions as R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 , R 1-1 , R 2- 1.
  • R 1-2 , R 2-2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , n1, n2 and n3 are as defined above Said, m1 and m2 are 0, 1, 2, 3 or 4 independently.
  • the present invention provides an application of a 1,3,5-triazine compound as shown in formula I as an electronic material.
  • the electronic material is used as an electron transport material and/or electron acceptor material; preferably an electron transport material and/or electron acceptor material in an organic electroluminescence device.
  • the invention provides an application of a 1,3,5-triazine compound represented by formula I in the field of organic electroluminescence devices.
  • the 1,3,5-triazine compound represented by formula I is used to prepare the electron transport layer, the hole blocking layer and the light emitting layer in an organic electroluminescent device One or more of.
  • the present invention provides an organic electroluminescent composition, which includes an electron donor material and the 1,3,5-triazine compound represented by formula I.
  • the electron donor material in the organic electroluminescence composition may be a conventional phenyl or naphthylcarbazole electron donor material in the art; the benzene
  • the phenyl or naphthylcarbazole type electron donor material preferably contains 2-3 phenylcarbazole or naphthylcarbazole group structures; the phenyl or naphthylcarbazole type electron donor material preferably Any of the following compounds:
  • the molar ratio of the 1,3,5-triazine compound shown in formula I and the electron donor material can be a conventional molar ratio in the art (for example, a conventional excitation in the art).
  • the molar ratio of the electron acceptor material to the electron donor material in the matrix composite), preferably, the 1,3,5-triazine compound shown in formula I and the electron donor material The molar ratio is 3:1 to 1:3; more preferably 1:1.
  • the organic electroluminescent composition may also include a doped luminescent material; the doped luminescent material may be a conventional doped luminescent material in the field, such as fluorescent light. Materials and/or phosphorescent luminescent materials (also called phosphorescent complex luminescent materials).
  • the mass percentage of the doped luminescent material in the organic electroluminescent composition can be a conventional mass percentage in the art.
  • the doped luminescent material is a fluorescent luminescent material
  • the The mass percentage of the doped luminescent material in the composition is preferably 0.5WT%-2.0WT% (for example, 1WT%); when the doped luminescent material is a phosphorescent luminescent material, the doped luminescent material
  • the mass percentage of the heteroluminescent material in the composition is preferably 5.0 WT% to 15.0 WT% (for example, 10 WT%).
  • the phosphorescent luminescent material in the doped luminescent material, may be a conventional phosphorescent luminescent material in the art. In the present invention, it is preferably any of the following compounds:
  • Ra 1 , Ra 3 , Rb 1 , Rb 3 , Rd 1 , Rd 3 , Re 4 , Re 5 , Re 6 , Rf 7 , Rf 8 , Rf 9 , Rb 10-1 , Rb 10-2 , Re 10 -1 , Re 10-2 , Rf 10-1 and Rf 10-2 are independently H or a linear or branched alkyl group containing 1-5 C;
  • Ra 2 , Rb 2 and Rd 2 are independently H, a linear or branched alkyl group containing 1 to 5 C, a phenyl group, or a phenyl substituted with a linear or branched chain alkyl group of 1 to 5 C;
  • the phosphorescent luminescent material in the doped luminescent material, is IrPPy 3
  • the fluorescent luminescent material in the doped luminescent material, may be a conventional fluorescent luminescent material in the art. In the present invention, it is preferably any of the following compounds:
  • Rg 11-1 , Rg 11-2 , Rh 11-1 , and Rh 11-2 are independently linear or branched alkyl groups containing 1-5 C;
  • Rg 12-1 , Rg 12-2 , Rh 13-1 , Rh 13-2 , Rh 13-3 and Rh 13-4 represent linear or branched alkyl groups containing 1-5 C, F or CF 3 ;
  • Rm 22-1 , Rn 25-1 , Ro 28-11 and Rp 33-1 are linear or branched alkyl groups containing 1-4 Cs.
  • the fluorescent luminescent material in the doped luminescent material, is
  • the present invention provides an application of the above-mentioned organic electroluminescent composition as an organic electroluminescent material.
  • the organic electroluminescent material is used to prepare the light-emitting layer in an organic electroluminescent device.
  • the present invention provides an organic electroluminescent device, which contains the organic electroluminescent composition as described above.
  • the organic electroluminescent composition is a light-emitting layer (the light-emitting principle of the light-emitting layer is based on the exciplex formed by electron donor molecules and electron acceptor molecules, namely molecules formed by Exciplex Charge transfer between excited states).
  • the organic electroluminescent device further includes a substrate, and an anode layer, an organic light-emitting functional layer, and a cathode layer sequentially formed on the substrate;
  • the organic light-emitting functional layer includes
  • the light-emitting layer as described above may also include any one or a combination of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer; preferably
  • the electron transport material in the electron transport layer has the same structure as the 1,3,5-triazine compound in the organic electroluminescence composition.
  • the invention provides an application of the organic electroluminescence device in an organic electroluminescence display or an organic electroluminescence illumination light source.
  • the number of the "substituted" can be one or more; when there are more than one, it can be 2, 3 or 4.
  • the “substitution” when the number of the "substitution" is multiple, the “substitution” may be the same or different.
  • the position of "substitution" can be any position unless otherwise specified.
  • the hydrogen or H is a hydrogen element in natural abundance, that is, a mixture of isotopes protium, deuterium and tritium, in which the abundance of protium is 99.98%.
  • the deuterium is D or 2 H, which is also called deuterium.
  • the abundance of deuterium at the deuterium substitution site is greater than 99%.
  • the term "containing” or “including (including)” can be open, semi-closed, and closed. In other words, the term also includes “substantially consisting of” or “consisting of”.
  • C 1 -C 6 alkyl refers to an alkyl group as defined below having a total of 1, 2, 3, 4, 5, or 6 carbon atoms.
  • the total number of carbon atoms in the simplified notation does not include carbons that may be present in the substituents of the group.
  • the numerical range defined in the substituents such as 0 to 4, 1-4, 1 to 3, etc., indicates an integer within the range, for example, 1-6 is 0, 1, 2, 3, 4, 5, 6.
  • halogen means fluorine, chlorine, bromine or iodine.
  • alkyl is meant to include branched and straight-chain chains with the specified number of carbon atoms Saturated aliphatic hydrocarbon group. For example, C 1 ⁇ C 10 . As defined in "C 1 -C 6 alkyl", it includes groups having 1, 2, 3, 4, 5, or 6 carbon atoms in a linear or branched structure.
  • the C 1 ⁇ C 6 alkyl groups are each independently methyl, ethyl, propyl, butyl, pentyl or hexyl; wherein, propyl is C 3 alkyl (including the same Isomers, such as n-propyl or isopropyl); butyl is C 4 alkyl (including isomers, such as n-butyl, sec-butyl, isobutyl or tert-butyl); pentyl is C 5 alkyl (including isomers, such as n-pentyl, 1-methyl-butyl, 1-ethyl-propyl, 2-methyl-1-butyl, 3-methyl-1- butyl, isopentyl, tert-pentyl or neopentyl); for the hexyl group C 6 alkyl group (including isomers, e.g. n-hexyl or isohexyl).
  • aryl refers to a monocyclic or polycyclic group having 6-14 ring atoms and zero heteroatoms provided in the aromatic ring system (E.g., bicyclic or tricyclic) 4n+2 aromatic ring system (e.g., having 6, 10, or 14 shared p electrons in a cyclic array) group ("C 6 ⁇ C 14 aryl) ").
  • aromatic ring system E.g., bicyclic or tricyclic
  • 4n+2 aromatic ring system e.g., having 6, 10, or 14 shared p electrons in a cyclic array
  • Examples of the aforementioned aryl unit include phenyl, naphthyl, phenanthryl, or anthracenyl.
  • heteroaryl refers to having ring carbon atoms and 1-4 ring heteroatoms provided in the aromatic ring system (where each hetero Atoms independently selected from nitrogen, oxygen and sulfur) 5-6 membered monocyclic or polycyclic (for example, bicyclic or tricyclic) 4n+2 aromatic ring system group ("5-6 member Heteroaryl").
  • Heteroaryl groups within the scope of this definition include but are not limited to: acridinyl, carbazolyl, cinnolinyl, quinoxalinyl, pyrazolyl, indolyl, benzotriazolyl, furyl, thienyl , Benzothienyl, benzofuranyl, quinolinyl, isoquinolinyl, oxazolyl, isoxazolyl, indolyl, pyrazinyl, pyridazinyl, pyridinyl, pyrimidinyl, pyrrolyl, Tetrahydroquinoline.
  • part refers to specific fragments or functional groups in a molecule.
  • the chemical moiety is generally considered to be a chemical entity embedded or attached to a molecule.
  • the present invention adopts traditional methods of mass spectrometry and elemental analysis, and the steps and conditions can refer to the conventional operating steps and conditions in the art.
  • the present invention adopts standard nomenclature and standard laboratory procedures and techniques of analytical chemistry, synthetic organic chemistry and optics. In some cases, standard techniques are used for chemical synthesis, chemical analysis, and performance testing of light-emitting devices.
  • the compounds of the present invention may contain unnatural proportions of atomic isotopes on one or more of the atoms constituting the compound.
  • compounds can be labeled with radioisotopes, such as deuterium ( 2 H). All changes in the isotopic composition of the compounds of the present invention, whether radioactive or not, are included in the scope of the present invention.
  • the reagents and raw materials used in the present invention are all commercially available.
  • the positive progress effect of the present invention is that: the substituted 1,3,5-triazine compound represented by formula I provided by the present invention has good electron accepting ability and electron transport ability; and has good thermal stability.
  • Such compounds can be used in the field of organic electroluminescence. It can be used alone as an electron transport layer or hole blocking layer, or combined with an electron donor material to form a composite host material, and used alone in an organic electroluminescent device.
  • This composite host material can be combined with some light-emitting materials (Including phosphorescent and fluorescent materials) Doping constructs the light-emitting layer of organic electroluminescent materials. Therefore, this material can be simultaneously used as a functional material in the light-emitting layer and electron transport layer/hole blocking layer of electroluminescent devices.
  • the electron transport layer and the electron acceptor material in the light-emitting layer belong to the same molecule.
  • the electrons enter the light-emitting layer from the electron transport layer there is no customer service barrier, which is beneficial to reduce the driving voltage and efficiency roll-off of the light-emitting device, and improve the efficiency and life of the device.
  • the molecular ion mass determined by mass spectrometry analysis is: 501.00 (calculated value: 501.20); theoretical element content (%) C 34 H 23 N 5 : C, 81.42; H, 4.62; N, 13.96; measured element content (%): C, 81.25; H, 4.60; N, 14.22.
  • the above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps were the same, and the compound 4-formylphenylboronic acid was used instead of the compound 2-formylphenylboronic acid to obtain 0.523 g of a white compound (yield 66.7%).
  • the molecular ion mass determined by mass spectrometry was 501.12 ( Calculated value: 501.20); theoretical element content (%) C 34 H 23 N 5 : C, 81.42; H, 4.62; N, 13.96; measured element content (%): C, 81.37; H, 4.60; N, 14.28 .
  • the above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps were the same, and the compound 3-formylphenylboronic acid was used instead of the compound 2-formylphenylboronic acid to obtain 0.632g of a white compound (yield 80.6%).
  • the molecular ion mass determined by mass spectrometry was 501.04( Calculated value: 501.20); theoretical element content (%) C 34 H 23 N 5 : C, 81.42; H, 4.62; N, 13.96; measured element content (%): C, 81.45; H, 4.65; N, 14.02 .
  • the above analysis results show that the obtained product is the target product.
  • the molecular ion mass determined by mass spectrometry analysis is: 501.12 (calculated value: 501.20); theoretical element content (%) C 34 H 23 N 5 : C, 81.42; H, 4.62; N, 13.96; measured element content (%): C, 81.35; H, 4.67; N, 14.03.
  • the above analysis results show that the obtained product is the target product.
  • Example 4 According to the synthesis of Example 4, the steps are the same, and the compound N-(3-bromophenyl)-1,2-phenylenediamine is substituted for the compound N-(4-bromophenyl)-1,2-phenylenediamine to obtain White compound 638 mg (yield 85.0%).
  • the molecular ion mass determined by mass spectrometry analysis is: 501.08 (calculated value: 501.20); theoretical element content (%) C 34 H 23 N 5 : C, 81.42; H, 4.62; N, 13.96; measured element content (%): C, 81.35; H, 4.55; N, 14.12.
  • the above analysis results show that the obtained product is the target product.
  • Example 4 According to the synthesis of Example 4, the steps are the same, and the compound N-(2-bromophenyl)-1,2-phenylenediamine is substituted for the compound N-(4-bromophenyl)-1,2-phenylenediamine to obtain 0.523g of white compound (yield 66.7%), the molecular ion mass determined by mass spectrometry analysis is: 501.32 (calculated value: 501.20); theoretical element content (%) C 34 H 23 N 5 : C, 81.42; H, 4.62; N, 13.96; Measured element content (%): C, 81.38; H, 4.57; N, 14.02. The above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps were the same, and the compound N-(3-pyridyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.553g of white compound (yield 70.5%), which was confirmed by mass spectrometry
  • the molecular ion mass of is: 502.28 (calculated value: 502.19); theoretical element content (%) C 33 H 22 N 6 : C, 78.87; H, 4.41; N, 16.72, measured element content (%): C, 78.95 ; H, 4.33; N, 16.85.
  • the above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps were the same, and the compound N-(4-pyridyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.356g of white compound (yield 45.4%), which was confirmed by mass spectrometry
  • the molecular ion mass of is: 502.31 (calculated value: 502.19); theoretical element content (%) C 33 H 22 N 6 : C, 78.87; H, 4.41; N, 16.72, measured element content (%): C, 78.95 ; H, 4.61; N, 16.63.
  • the above analysis results show that the obtained product is the target product.
  • Example 3 According to the synthesis of Example 3, the steps were the same, and the compound N-(3-pyridyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.435g of white compound (yield 55.5%), which was confirmed by mass spectrometry
  • the molecular ion mass of is: 502.20 (calculated value: 502.19); theoretical element content (%) C 33 H 22 N 6 : C, 78.87; H, 4.41; N, 16.72, measured element content (%): C, 78.85 ; H, 4.41; N, 16.83.
  • the above analysis results show that the obtained product is the target product.
  • Example 3 According to the synthesis of Example 3, the steps were the same, the compound N-(4-pyridyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.398g of white compound (yield 50.8%), which was confirmed by mass spectrometry
  • the molecular ion mass of is: 502.18 (calculated value: 502.19); theoretical element content (%) C 33 H 22 N 6 : C, 78.87; H, 4.41; N, 16.72, measured element content (%): C, 78.88 ; H, 4.49; N, 16.81.
  • the above analysis results show that the obtained product is the target product.
  • Example 2 According to the synthesis of Example 2, the steps are the same, the compound N-(3-pyridyl)-1,2-phenylenediamine is used instead of the compound o-aminodiphenylamine to obtain 0.444g of white compound (yield 56.6%), which is confirmed by mass spectrometry
  • the molecular ion mass of is: 502.08 (calculated value: 502.19); theoretical element content (%) C 33 H 22 N 6 : C, 78.87; H, 4.41; N, 16.72, measured element content (%): C, 78.98 ; H, 4.28; N, 16.77.
  • the above analysis results show that the obtained product is the target product.
  • Example 2 According to the synthesis of Example 2, the steps were the same, and the compound N-(4-pyridyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.466g of white compound (yield 59.4%), which was confirmed by mass spectrometry
  • the molecular ion mass of is: 502.18 (calculated value: 502.19); theoretical element content (%) C 33 H 22 N 6 : C, 78.87; H, 4.41; N, 16.72, measured element content (%): C, 78.95 ; H, 4.61; N, 16.83.
  • the above analysis results show that the obtained product is the target product.
  • Example 6 According to the synthesis of Example 6, the steps were the same, and the compound 3-aldehyde pyridine was used instead of the compound benzaldehyde to obtain 0.425 g of a white compound (yield 54.2%).
  • the molecular ion mass determined by mass spectrometry was 502.13 (calculated value: 502.19). );
  • Theoretical element content (%) C 33 H 22 N 6 C, 78.87; H, 4.41; N, 16.72, the measured element content (%): C, 78.89; H, 4.21; N, 16.93.
  • the above analysis results show that the obtained product is the target product.
  • Example 6 According to the synthesis of Example 6, the steps were the same, and the compound 4-aldehyde pyridine was used instead of the compound benzaldehyde to obtain 0.289 g of a white compound (yield 36.9%).
  • the molecular ion mass determined by mass spectrometry was 502.22 (calculated value: 502.29). );
  • Theoretical element content (%) C 33 H 22 N 6 C, 78.87; H, 4.41; N, 16.72, the measured element content (%): C, 78.89; H, 4.22; N, 16.90.
  • the above analysis results show that the obtained product is the target product.
  • Example 5 According to the synthesis of Example 5, the steps were the same, and the compound 3-aldehyde pyridine was used instead of the compound benzaldehyde to obtain 0.333 g of the white compound (yield 42.5%).
  • the mass of the molecular ion determined by mass spectrometry was 502.22 (calculated value: 502.29). );
  • Theoretical element content (%) C 33 H 22 N 6 C, 78.87; H, 4.41; N, 16.72, the measured element content (%): C, 78.86; H, 4.40; N, 16.81.
  • the above analysis results show that the obtained product is the target product.
  • Example 5 According to the synthesis of Example 5, the steps were the same, and the compound 4-aldehyde pyridine was used instead of the compound benzaldehyde to obtain 0.259 g of the white compound (yield 33.0%).
  • the mass of the molecular ion determined by mass spectrometry was: 502.23 (calculated value: 502.29) );
  • Theoretical element content (%) C 33 H 22 N 6 C, 78.87; H, 4.41; N, 16.72, the measured element content (%): C, 78.87; H, 4.51; N, 16.87.
  • the above analysis results show that the obtained product is the target product.
  • Example 4 According to the synthesis of Example 4, the steps were the same, and the compound 3-aldehyde pyridine was used instead of the compound benzaldehyde to obtain 0.295 g of a white compound (yield 37.7%).
  • the molecular ion mass determined by mass spectrometry was 502.15 (calculated value: 502.19). );
  • Theoretical element content (%) C 33 H 22 N 6 C, 78.87; H, 4.41; N, 16.72, the measured element content (%): C, 78.75; H, 4.21; N, 16.73.
  • the above analysis results show that the obtained product is the target product.
  • Example 4 According to the synthesis of Example 4, the steps were the same, and the compound 4-aldehyde pyridine was used instead of the compound benzaldehyde to obtain 0.318 g of a white compound (yield 40.6%).
  • the molecular ion mass determined by mass spectrometry analysis was: 502.18 (calculated value: 502.19) );
  • Theoretical element content (%) C 33 H 22 N 6 C, 78.87; H, 4.41; N, 16.72, the measured element content (%): C, 78.88; H, 4.42; N, 16.84.
  • the above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps are the same, and the compound N 1 -(2-fluorophenyl)-1,2-phenylenediamine is used instead of the compound o-aminodiphenylamine to obtain 0.523 g of a white compound (yield 68.2%), mass spectrum
  • the molecular ion mass determined by analysis is: 519.28 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.55; H, 4.24; F, 3.69; N, 13.41.
  • the above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps were the same, and the compound N 1 -(3-fluorophenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.512 g of white compound (yield 65.6%), mass spectrum
  • the molecular ion mass determined by analysis is: 519.33 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C,78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.57; H, 4.26; F, 3.71; N, 13.43.
  • the above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps were the same, and the compound N 1 -(4-fluorophenyl)-1,2-phenylenediamine was used instead of the o-aminodiphenylamine compound to obtain 0.502 g of a white compound (yield 64.4%), mass spectrum
  • the molecular ion mass determined by analysis is: 519.09 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.55; H, 4.24; F, 3.69; N, 13.41.
  • the above analysis results show that the obtained product is the target product.
  • Example 3 According to the synthesis of Example 3, the steps were the same, and the compound N 1 -(2-fluorophenyl)-1,2-phenylenediamine was used instead of the o-aminodiphenylamine compound to obtain 0.488 g of the white compound (yield 62.6%).
  • Mass spectrum The molecular ion mass determined by analysis is: 519.29 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.57; H, 4.23; F, 3.68; N, 13.40.
  • the above analysis results show that the obtained product is the target product.
  • Example 3 According to the synthesis of Example 3, the steps were the same, the compound N 1 -(3-fluorophenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.532g of a white compound (yield 68.2%), mass spectrum
  • the molecular ion mass determined by analysis is: 519.11 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C,78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.66; H, 4.34; F, 3.79; N, 13.51.
  • the above analysis results show that the obtained product is the target product.
  • Example 3 According to the synthesis of Example 3, the steps were the same, and the compound N 1 -(4-fluorophenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.449 g of a white compound (yield 57.6%), mass spectrum
  • the molecular ion mass determined by analysis is: 519.05 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C,78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.75; H, 4.34; F, 3.60; N, 13.43.
  • the above analysis results show that the obtained product is the target product.
  • Example 2 According to the synthesis of Example 2, the steps are the same, and the compound N 1 -(2-fluorophenyl)-1,2-phenylenediamine is used instead of the compound o-aminodiphenylamine to obtain 0.439 g of a white compound (yield 56.7%), mass spectrum
  • the molecular ion mass determined by analysis is: 519.11 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C,78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.55; H, 4.24; F, 3.69; N, 13.41.
  • the above analysis results show that the obtained product is the target product.
  • Example 2 According to the synthesis of Example 2, the steps are the same, the compound N 1 -(3-fluorophenyl)-1,2-phenylenediamine is used instead of the compound o-aminodiphenylamine to obtain 0.429 g of a white compound (yield 55.0%), mass spectrum
  • the molecular ion mass determined by analysis is: 519.13 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.66; H, 4.34; F, 3.64; N, 13.45.
  • the above analysis results show that the obtained product is the target product.
  • Example 3 According to the synthesis of Example 3, the steps were the same, and the compound N 1 -(4-fluorophenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.563 g of a white compound (yield 72.2%), mass spectrum
  • the molecular ion mass determined by analysis is: 519.22 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C,78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.57; H, 4.22; F, 3.67; N, 13.51.
  • the above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps were the same, and the compound N 1 -(3,5-difluorophenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.537g of a white compound (yield 66.7%) ), the molecular ion mass determined by mass spectrometry analysis is: 537.28 (calculated value: 537.18); theoretical element content (%) C 34 H 21 F 2 N 5 : C, 75.97; H, 3.94; F, 7.07; N, 13.03 , Measured element content (%): C, 76.07; H, 3.99; F, 7.17; N, 13.08. The above analysis results show that the obtained product is the target product.
  • Example 3 According to the synthesis of Example 3, the steps are the same, the compound N 1 -(3,5-difluorophenyl)-1,2-phenylenediamine is used instead of the compound o-aminodiphenylamine to obtain 0.454g of a white compound (yield 56.2%) ), the molecular ion mass determined by mass spectrometry analysis is: 537.20 (calculated value: 537.18); theoretical element content (%) C 34 H 21 F 2 N 5 : C, 75.97; H, 3.94; F, 7.07; N, 13.03 , Measured element content (%): C, 76.00; H, 4.10; F, 7.07; N, 13.18. The above analysis results show that the obtained product is the target product.
  • Example 2 According to the synthesis of Example 2, the steps were the same, and the compound N 1 -(3,5-difluorophenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.390g of a white compound (yield 48.3%) ), the molecular ion mass determined by mass spectrometry analysis is: 537.09 (calculated value: 537.18); theoretical element content (%) C 34 H 21 F 2 N 5 : C, 75.97; H, 3.94; F, 7.07; N, 13.03 , Measured element content (%): C, 75.99; H, 3.92; F, 7.09; N, 13.13. The above analysis results show that the obtained product is the target product.
  • Example 6 According to the synthesis of Example 6, the steps were the same, and the compound 2-fluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.392 g of a white compound (yield 50.2%).
  • the mass of molecular ion determined by mass spectrometry was 519.24 (calculated value: 519.19) );
  • Theoretical element content (%) C 34 H 22 FN 5 C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content (%): C, 78.55; H, 4.29; F, 3.69; N, 13.33.
  • the above analysis results show that the obtained product is the target product.
  • Example 5 According to the synthesis of Example 5, the steps were the same, and the compound 2-fluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.353 g of a white compound (yield 45.3%).
  • the molecular ion mass determined by mass spectrometry was 519.15 (calculated value: 519.19) );
  • Theoretical element content (%) C 34 H 22 FN 5 C, 78.60; H, 4.27; F, 3.66; N, 13.48, the measured element content (%): C, 78.66; H, 4.22; F, 3.69; N, 13.59.
  • the above analysis results show that the obtained product is the target product.
  • Example 4 According to the synthesis of Example 4, the steps were the same, and the compound 2-fluorobenzaldehyde was substituted for the compound benzaldehyde to obtain 0.357 g of a white compound (yield 45.8%).
  • the mass of molecular ion determined by mass spectrometry was 519.22 (calculated value: 519.19) );
  • Theoretical element content (%) C 34 H 22 FN 5 C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content (%): C, 78.59; H, 4.32; F, 3.77; N, 13.61.
  • the above analysis results show that the obtained product is the target product.
  • Example 6 According to the synthesis of Example 6, the steps were the same, and the compound 3-fluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.405 g of a white compound (yield 51.9%).
  • the molecular ion mass determined by mass spectrometry was 519.15 (calculated value: 519.19) );
  • Theoretical element content (%) C 34 H 22 FN 5 C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content (%): C, 78.62; H, 4.28; F, 3.69; N, 13.59.
  • the above analysis results show that the obtained product is the target product.
  • Example 5 According to the synthesis of Example 5, the steps were the same, and the compound 3-fluorobenzaldehyde was substituted for the compound benzaldehyde to obtain 0.416 g of a white compound (yield 53.3%).
  • the mass of the molecular ion determined by mass spectrometry was 519.28 (calculated value: 519.19) );
  • Theoretical element content (%) C 34 H 22 FN 5 C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content (%): C, 78.67; H, 4.42; F, 3.47; N, 13.41.
  • the above analysis results show that the obtained product is the target product.
  • Example 4 According to the synthesis of Example 4, the steps were the same, and the compound 3-fluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.523 g of a white compound (yield 66.7%).
  • the molecular ion mass determined by mass spectrometry was 519.22 (calculated value: 519.19) );
  • Theoretical element content (%) C 34 H 22 FN 5 C, 78.60; H, 4.27; F, 3.66; N, 13.48, the measured element content (%): C, 78.57; H, 4.22; F, 3.67; N, 13.51.
  • the above analysis results show that the obtained product is the target product.
  • Example 6 According to the synthesis of Example 6, the steps were the same, and the compound 4-fluorobenzaldehyde was substituted for the compound benzaldehyde to obtain 0.435 g of a white compound (yield 55.8%).
  • the mass of the molecular ion determined by mass spectrometry was 519.25 (calculated value: 519.19) );
  • Theoretical element content (%) C 34 H 22 FN 5 C, 78.60; H, 4.27; F, 3.66; N, 13.48, the measured element content (%): C, 78.57; H, 4.22; F, 3.67; N, 13.51.
  • the above analysis results show that the obtained product is the target product.
  • Example 5 According to the synthesis of Example 5, the steps were the same, and the compound 4-fluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.472 g of a white compound (yield 60.5%).
  • the molecular ion mass determined by mass spectrometry was 519.10 (calculated value: 519.19) );
  • Theoretical element content (%) C 34 H 22 FN 5 C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content (%): C, 78.58; H, 4.22; F, 3.87; N, 13.51.
  • the above analysis results show that the obtained product is the target product.
  • Example 4 According to the synthesis of Example 4, the steps were the same, and the compound 4-fluorobenzaldehyde was substituted for the compound benzaldehyde to obtain 0.416 g of a white compound (yield 53.4%).
  • the molecular ion mass determined by mass spectrometry was 519.14 (calculated value: 519.19) );
  • Theoretical element content (%) C 34 H 22 FN 5 C, 78.60; H, 4.27; F, 3.66; N, 13.48, the measured element content (%): C, 78.77; H, 4.12; F, 3.87; N, 13.51.
  • the above analysis results show that the obtained product is the target product.
  • Example 6 According to the synthesis of Example 6, the steps were the same, and the compound 3,5-difluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.361 g of a white compound (yield 44.9%).
  • the molecular ion mass determined by mass spectrometry was 537.33 (calculated value) Is: 537.18); theoretical element content (%) C 34 H 21 F 2 N 5 : C, 75.97; H, 3.94; F, 7.07; N, 13.03, measured element content (%): C, 76.07; H, 3.99 ; F,7.17; N,13.08.
  • the above analysis results show that the obtained product is the target product.
  • Example 5 According to the synthesis of Example 5, the steps were the same, and the compound 3,5-difluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.382g of a white compound (yield 47.5%).
  • the molecular ion mass determined by mass spectrometry was 537.19 (calculated value) Is: 537.18); theoretical element content (%) C 34 H 21 F 2 N 5 : C, 75.97; H, 3.94; F, 7.07; N, 13.03, measured element content (%): C, 75.87; H, 4.12 ; F, 7.07; N, 13.18.
  • the above analysis results show that the obtained product is the target product.
  • Example 4 According to the synthesis of Example 4, the steps are the same, and the compound 3,5-difluorobenzaldehyde is used instead of the compound benzaldehyde to obtain 0.425g of white compound (yield 52.8%).
  • the mass of molecular ion determined by mass spectrometry is 537.09 (calculated value) Is: 537.18); theoretical element content (%) C 34 H 21 F 2 N 5 : C, 75.97; H, 3.94; F, 7.07; N, 13.03, measured element content (%): C, 76.11; H, 3.89 ; F, 7.25; N, 13.18.
  • the above analysis results show that the obtained product is the target product.
  • Example 7 According to the synthesis of Example 7, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.553g of white compound was obtained (yield 51.2%), the molecular ion mass determined by mass spectrometry was 538.25 (calculated value: 538.17); theoretical element content (%) C 33 H 20 F 2 N 6 : C, 73.60; H, 3.74; F, 7.06; N, 15.60, measured element content (%): C, 73.58; H, 3.81; F, 7.16; N, 15.77. The above analysis results show that the obtained product is the target product.
  • Example 8 According to the synthesis of Example 8, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.657g of white compound was obtained (yield 60.8%), the molecular ion mass determined by mass spectrometry analysis was: 538.32 (calculated value: 538.17); theoretical element content (%) C 33 H 20 F 2 N 6 : C, 73.60; H, 3.74; F, 7.06; N, 15.60, measured element content (%): C, 73.49; H, 3.83; F, 7.11; N, 15.53. The above analysis results show that the obtained product is the target product.
  • Example 9 According to the synthesis of Example 9, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.619g of white compound was obtained (yield 57.3%), the molecular ion mass determined by mass spectrometry analysis was: 538.33 (calculated value: 538.17); theoretical element content (%) C 33 H 20 F 2 N 6 : C, 73.60; H, 3.74; F, 7.06; N, 15.60, measured element content (%): C, 73.59; H, 3.77; F, 7.26; N, 15.58. The above analysis results show that the obtained product is the target product.
  • Example 10 According to the synthesis of Example 10, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.511g of white compound was obtained (yield 47.3%), the molecular ion mass determined by mass spectrometry analysis was: 538.09 (calculated value: 538.17); theoretical element content (%) C 33 H 20 F 2 N 6 : C, 73.60; H, 3.74; F, 7.06; N, 15.60, measured element content (%): C, 73.55; H, 3.80; F, 7.14; N, 15.77. The above analysis results show that the obtained product is the target product.
  • Example 11 According to the synthesis of Example 11, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine to obtain 0.597g of white compound (yield 55.3%), the molecular ion mass determined by mass spectrometry analysis is: 538.30 (calculated value: 538.17); theoretical element content (%) C 33 H 20 F 2 N 6 : C, 73.60; H, 3.74; F, 7.06; N, 15.60, measured element content (%): C, 73.47; H, 3.59; F, 7.21; N, 15.46. The above analysis results show that the obtained product is the target product.
  • Example 12 According to the synthesis of Example 12, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.517g of white compound was obtained (yield 47.9%), the mass of molecular ion determined by mass spectrometry was 538.22 (calculated value: 538.17); theoretical element content (%) C 33 H 20 F 2 N 6 : C, 73.60; H, 3.74; F, 7.06; N, 15.60, measured element content (%): C, 73.60; H, 3.77; F, 7.16; N, 15.49.
  • the above analysis results show that the obtained product is the target product.
  • the molecular ion mass determined by mass spectrometry analysis is: 693.15 (calculated value: 693.26); theoretical element content (%) C 47 H 31 N 7 : C, 81.36; H, 4.50; N, 14.13; measured element content (%): C, 81.25; H, 4.60; N, 14.22.
  • the above analysis results show that the obtained product is the target product.
  • the molecular ion mass determined by mass spectrometry analysis is: 693.18 (calculated value: 693.26); theoretical element content (%) C 47 H 31 N 7 : C, 81.36; H, 4.50; N, 14.13; measured element content (%): C, 81.50; H, 4.65; N, 14.03.
  • the above analysis results show that the obtained product is the target product.
  • Example 49 According to the synthesis of Example 49, the steps were the same, and the compound N-(3-pyridyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.716g of white compound (yield 68.9%), which was confirmed by mass spectrometry
  • the molecular ion mass of is: 695.33 (calculated value: 695.25); theoretical element content (%) C 45 H 29 N 9 : C,77.68; H, 4.20; N, 18.12, measured element content (%): C,77.77 ; H, 4.15; N, 18.35.
  • the above analysis results show that the obtained product is the target product.
  • Example 49 According to the synthesis of Example 49, the steps were the same, the compound N-(4-pyridyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.557g of white compound (yield 53.6%), which was confirmed by mass spectrometry
  • the molecular ion mass of is: 695.33 (calculated value: 695.25); theoretical element content (%) C 45 H 29 N 9 : C,77.68; H, 4.20; N, 18.12, measured element content (%): C,77.73 ; H, 4.17; N, 18.19.
  • the above analysis results show that the obtained product is the target product.
  • Example 50 According to the synthesis of Example 50, the steps were the same, and the compound 3-aldehyde pyridine was used instead of the compound benzaldehyde to obtain 0.474 g of a white compound (yield 45.6%).
  • the molecular ion mass determined by mass spectrometry was 695.46 (calculated value: 695.25) );
  • Theoretical element content (%) C 45 H 29 N 9 C, 77.68; H, 4.20; N, 18.12, the measured element content (%): C, 77.70; H, 4.14; N, 18.28.
  • the above analysis results show that the obtained product is the target product.
  • Example 50 According to the synthesis of Example 50, the steps were the same, and the compound 4-aldehyde pyridine was used instead of the compound benzaldehyde to obtain 0.547 g (yield of 52.6%) of a white compound.
  • the molecular ion mass determined by mass spectrometry was 695.24 (calculated value: 695.25) );
  • Theoretical element content (%) C 45 H 29 N 9 C, 77.68; H, 4.20; N, 18.12, the measured element content (%): C, 77.73; H, 4.11; N, 18.20.
  • the above analysis results show that the obtained product is the target product.
  • Example 49 According to the synthesis of Example 49, the steps are the same, using compound N 1 ,N 1 '- ⁇ 5-bromo-1,3-bis(2-fluorophenyl) ⁇ bis(1,2-phenylenediamine) instead of compound N 1 ,N 1 '-(5-bromo-1,3-diphenyl)bis(1,2-phenylenediamine), 0.504g of white compound (yield 46.2%) is obtained, and the molecular ion mass determined by mass spectrometry is : 729.33 (calculated value: 729.25); theoretical element content (%) C 47 H 29 F 2 N 7 : C, 77.35; H, 4.01; F, 5.21; N, 13.44, measured element content (%): C, 77.42; H, 4.07; F, 5.31; N, 13.52.
  • the above analysis results show that the obtained product is the target product.
  • Example 49 According to the synthesis of Example 49, the steps are the same, using compound N 1 ,N 1 '- ⁇ 5-bromo-1,3-bis(2-fluorophenyl) ⁇ bis(1,2-phenylenediamine) instead of compound N 1 ,N 1 '-(5-bromo-1,3-diphenyl)bis(1,2-phenylenediamine), 0.560g of white compound (yield 51.4%) was obtained, and the molecular ion mass determined by mass spectrometry was : 729.11 (calculated value: 729.25); theoretical element content (%) C 47 H 29 F 2 N 7 : C, 77.35; H, 4.01; F, 5.21; N, 13.44, measured element content (%): C, 77.33; H, 4.11; F, 5.23; N, 13.56.
  • the above analysis results show that the obtained product is the target product.
  • Example 49 According to the synthesis of Example 49, the steps are the same, using compound N 1 ,N 1 '- ⁇ 5-bromo-1,3-bis(2-fluorophenyl) ⁇ bis(1,2-phenylenediamine) instead of compound N 1 ,N 1 '-(5-bromo-1,3-diphenyl)bis(1,2-phenylenediamine), 0.597g of white compound (yield 54.8%) was obtained, and the molecular ion mass determined by mass spectrometry was : 729.23 (calculated value: 729.25); theoretical element content (%) C 47 H 29 F 2 N 7 : C, 77.35; H, 4.01; F, 5.21; N, 13.44, measured element content (%): C, 77.51; H, 4.12; F, 5.16; N, 13.50.
  • the above analysis results show that the obtained product is the target product.
  • Example 50 According to the synthesis of Example 50, the steps were the same, and the compound 2-fluorobenzaldehyde was substituted for the compound benzaldehyde to obtain 0.560 g of a white compound (yield 51.4%).
  • the molecular ion mass determined by mass spectrometry was 729.31 (calculated value: 729.25) ); theoretical element content (%) C 47 H 29 F 2 N 7 : C, 77.35; H, 4.01; F, 5.21; N, 13.44, measured element content (%): C, 77.46; H, 4.26; F, 5.22; N, 13.47.
  • the above analysis results show that the obtained product is the target product.
  • Example 50 According to the synthesis of Example 50, the steps were the same, and the compound 3-fluorobenzaldehyde was substituted for the compound benzaldehyde to obtain 0.517 g of a white compound (yield 47.4%).
  • the molecular ion mass determined by mass spectrometry was 729.51 (calculated value: 729.25) );
  • the above analysis results show that the obtained product is the target product.
  • Example 50 According to the synthesis of Example 50, the procedure was the same, and the compound 4-fluorobenzaldehyde was substituted for the compound benzaldehyde to obtain 0.577 g of a white compound (yield 52.8%).
  • the molecular ion mass determined by mass spectrometry was 729.25 (calculated value: 729.25) );
  • the above analysis results show that the obtained product is the target product.
  • Example 49 According to the synthesis of Example 49, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine to obtain 0.511 g of a white compound (yield 46.6%).
  • the molecular ion mass determined by mass spectrometry analysis is: 729.50 (calculated value: 729.25); theoretical element content (%) C 47 H 29 F 2 N 7 : C, 77.35; H, 4.01; F, 5.21; N, 13.44, measured element content (%): C, 77.42; H, 3.99; F, 5.21; N, 13.40.
  • the above analysis results show that the obtained product is the target product.
  • Example 50 According to the synthesis of Example 50, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.573g of white compound was obtained (yield 52.3%), the molecular ion mass determined by mass spectrometry analysis was 729.33 (calculated value: 729.25); theoretical element content (%) C 47 H 29 F 2 N 7 : C, 77.35; H, 4.01; F, 5.21; N, 13.44, measured element content (%): C, 77.42; H, 4.12; F, 5.18; N, 13.33.
  • the above analysis results show that the obtained product is the target product.
  • Example 51 According to the synthesis of Example 51, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.502g of white compound was obtained (yield 45.8%), the molecular ion mass determined by mass spectrometry analysis was: 731.17 (calculated value: 731.24); theoretical element content (%) C 45 H 27 F 2 N 9 : C, 73.86; H, 3.72; F, 5.19; N, 17.23, measured element content (%): C, 73.93; H, 3.88; F, 5.21; N, 17.25. The above analysis results show that the obtained product is the target product.
  • Example 52 According to the synthesis of Example 52, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.505g of white compound was obtained (yield 46.1%), the molecular ion mass determined by mass spectrometry analysis was: 731.11 (calculated value: 731.24); theoretical element content (%) C 45 H 27 F 2 N 9 : C, 73.86; H, 3.72; F, 5.19; N, 17.23, measured element content (%): C, 73.90; H, 3.88; F, 5.22; N, 17.31. The above analysis results show that the obtained product is the target product.
  • Example 53 According to the synthesis of Example 53, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.523g of white compound was obtained (yield 66.7%), the molecular ion mass determined by mass spectrometry was 731.24 (calculated value: 731.24); theoretical element content (%) C 45 H 27 F 2 N 9 : C, 73.86; H, 3.72; F, 5.19; N, 17.23, measured element content (%): C, 73.86; H, 3.72; F, 5.19; N, 17.23.
  • the above analysis results show that the obtained product is the target product.
  • Example 54 According to the synthesis of Example 54, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine to obtain 0.771g of white compound (yield 52.8%), the molecular ion mass determined by mass spectrometry analysis is: 731.33 (calculated value: 731.24); theoretical element content (%) C 45 H 27 F 2 N 9 : C, 73.86; H, 3.72; F, 5.19; N, 17.23, measured element content (%): C, 73.96H, 3.88; F, 5.21; N, 17.25.
  • the above analysis results show that the obtained product is the target product.
  • Example 55 According to the synthesis of Example 55, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.744g white compound was obtained (yield 48.6%), the molecular ion mass determined by mass spectrometry analysis was 765.12 (calculated value: 765.23); theoretical element content (%) C 47 H 27 F 4 N 7 : C, 73.72; H, 3.55; F, 9.92; N, 12.80, measured element content (%): C, 73.68; H, 3.46; F, 9.80; N, 12.79. The above analysis results show that the obtained product is the target product.
  • Example 56 According to the synthesis of Example 56, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.635g of white compound was obtained (yield 41.5%), the molecular ion mass determined by mass spectrometry analysis was 765.23 (calculated value: 765.23); theoretical element content (%) C 47 H 27 F 4 N 7 : C, 73.72; H, 3.55; F, 9.92; N, 12.80, measured element content (%): C, 73.68; H, 3.66; F, 9.81; N, 12.77. The above analysis results show that the obtained product is the target product.
  • Example 57 According to the synthesis of Example 57, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.786g of white compound was obtained (yield 51.4%), the molecular ion mass determined by mass spectrometry analysis was 765.20 (calculated value: 765.23); theoretical element content (%) C 47 H 27 F 4 N 7 : C, 73.72; H, 3.55; F, 9.92; N, 12.80, measured element content (%): C, 73.68; H, 3.47; F, 9.88; N, 12.76. The above analysis results show that the obtained product is the target product.
  • Example 58 According to the synthesis of Example 58, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.770g of white compound was obtained (yield 50.3%), the molecular ion mass determined by mass spectrometry was 765.12 (calculated value: 765.23); theoretical element content (%) C 47 H 27 F 4 N 7 : C, 73.72; H, 3.55; F, 9.92; N, 12.80, measured element content (%): C, 73.86; H, 3.39; F, 9.79; N, 12.77.
  • the above analysis results show that the obtained product is the target product.
  • Example 59 According to the synthesis of Example 59, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.762g of white compound (yield 49.8%) was obtained.
  • the molecular ion mass determined by mass spectrometry analysis was 765.34 (calculated value: 765.23); theoretical element content (%) C 47 H 27 F 4 N 7 : C, 73.72; H, 3.55; F, 9.92; N, 12.80, measured element content (%): C, 73.62; H, 3.57; F, 9.88; N, 12.93.
  • the above analysis results show that the obtained product is the target product.
  • Example 60 According to the synthesis of Example 60, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.808g of white compound was obtained (yield 52.8%), the molecular ion mass determined by mass spectrometry analysis was 765.44 (calculated value: 765.23); theoretical element content (%) C 47 H 27 F 4 N 7 : C, 73.72; H, 3.55; F, 9.92; N, 12.80, measured element content (%): C, 73.68; H, 3.63; F, 9.94; N, 12.77. The above analysis results show that the obtained product is the target product.
  • Example 29 According to the synthesis of Example 29, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.606g of white compound was obtained (yield 52.9%), the molecular ion mass determined by mass spectrometry analysis was: 573.22 (calculated value: 573.16); theoretical element content (%) C 34 H 19 F 4 N 5 : C, 71.20; H, 3.34; F, 13.25; N, 12.21, measured element content (%): C, 71.24; H, 3.33; F, 13.36N, 12.31. The above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps were the same, and the compound N 1 -(3-trifluoromethylphenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.498g of a white compound (yield 58.3%) ), the molecular ion mass determined by mass spectrometry analysis is: 569.32 (calculated value: 569.18); theoretical element content (%) C 35 H 22 F 3 N 5 : C, 73.80; H, 3.89; F, 10.01; N, 12.30 Measured element content (%): C, 73.77; H, 3.92; F, 10.11; N, 12.35. The above analysis results show that the obtained product is the target product.
  • Example 3 According to the synthesis of Example 3, the steps were the same, and the compound N 1 -(3-trifluoromethylphenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.532g of a white compound (yield 53.2%) ), the molecular ion mass determined by mass spectrometry analysis is: 569.12 (calculated value: 569.18); theoretical element content (%) C 35 H 22 F 3 N 5 : C, 73.80; H, 3.89; F, 10.01; N, 12.30 Measured element content (%): C, 73.87; H, 3.91; F, 10.10; N, 12.31. The above analysis results show that the obtained product is the target product.
  • Example 2 According to the synthesis of Example 2, the steps were the same, and the compound N 1 -(3-trifluoromethylphenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.527 g of a white compound (yield 61.7%) ), the molecular ion mass determined by mass spectrometry analysis is: 569.33 (calculated value: 569.18); theoretical element content (%) C 35 H 22 F 3 N 5 : C, 73.80; H, 3.89; F, 10.01; N, 12.30 Measured element content (%): C, 73.91; H, 3.88; F, 10.06; N, 12.27. The above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps are the same, and the compound N 1 -(3,5-bis(trifluoromethyl)phenyl)-1,2-phenylenediamine is substituted for the compound o-aminodiphenylamine to obtain 0.524g of a white compound (Yield 54.8%), the molecular ion mass determined by mass spectrometry analysis is: 637.22 (calculated value: 637.17); theoretical element content (%) C 36 H 21 F 6 N 5 : C, 67.82; H, 3.32; F, 17.88; N, 10.98, measured element content (%): C, 67.77; H, 3.35; F, 17.90; N, 10.87.
  • the above analysis results show that the obtained product is the target product.
  • Example 3 According to the synthesis of Example 3, the steps are the same, the compound N 1 -(3,5-bis(trifluoromethyl)phenyl)-1,2-phenylenediamine is substituted for the compound o-aminodiphenylamine to obtain 0.524g of a white compound (Yield 54.8%), the molecular ion mass determined by mass spectrometry analysis is: 637.20 (calculated value: 637.17); theoretical element content (%) C 36 H 21 F 6 N 5 : C, 67.82; H, 3.32; F, 17.88; N, 10.98, measured element content (%): C, 67.87; H, 3.45; F, 17.82; N, 10.97.
  • the above analysis results show that the obtained product is the target product.
  • Example 2 According to the synthesis of Example 2, the steps are the same, and the compound N 1 -(3,5-bis(trifluoromethyl)phenyl)-1,2-phenylenediamine is substituted for the compound o-aminodiphenylamine to obtain 0.585g of a white compound (Yield 61.2%), the molecular ion mass determined by mass spectrometry analysis is: 637.15 (calculated value: 637.17); theoretical element content (%) C 36 H 21 F 6 N 5 : C, 67.82; H, 3.32; F, 17.88; N, 10.98, measured element content (%): C, 67.87; H, 3.36; F, 17.89; N, 10.94.
  • the above analysis results show that the obtained product is the target product.
  • Example 4 According to the synthesis of Example 4, the steps were the same, and the compound 3-trifluoromethylbenzaldehyde was used instead of the compound benzaldehyde to obtain 0.500 g of a white compound (yield 58.6%).
  • the molecular ion mass determined by mass spectrometry was 569.19 (calculated value) Is: 569.18); theoretical element content (%) C 35 H 22 F 3 N 5 : C, 73.80; H, 3.89; F, 10.01; N, 12.30; measured element content (%): C, 73.88; H, 3.83 ; F, 10.14; N, 12.34.
  • the above analysis results show that the obtained product is the target product.
  • Example 6 According to the synthesis of Example 6, the steps are the same, and the compound 3-trifluoromethylbenzaldehyde is used instead of the compound benzaldehyde to obtain 0.523g of a white compound (yield 66.7%).
  • the molecular ion mass determined by mass spectrometry is 569.33 (calculated value) Is: 569.18); theoretical element content (%) C 35 H 22 F 3 N 5 : C, 73.80; H, 3.89; F, 10.01; N, 12.30; measured element content (%): C, 73.91; H, 3.88 ; F, 10.06; N, 12.27.
  • the above analysis results show that the obtained product is the target product.
  • Example 5 According to the synthesis of Example 5, the steps were the same, and the compound 3-trifluoromethylbenzaldehyde was used instead of the compound benzaldehyde to obtain 0.516g of a white compound (yield 60.4%).
  • the mass of the molecular ion determined by mass spectrometry was 569.23 (calculated value) Is: 569.18); theoretical element content (%) C 35 H 22 F 3 N 5 : C, 73.80; H, 3.89; F, 10.01; N, 12.30; measured element content (%): C, 73.82; H, 3.85 ; F, 10.14; N, 12.33.
  • the above analysis results show that the obtained product is the target product.
  • Example 5 According to the synthesis of Example 5, the steps are the same, and the compound 3,5-bis(trifluoromethyl)benzaldehyde is used instead of the compound benzaldehyde to obtain 0.454g of white compound (yield 47.5%).
  • the mass of the molecular ion determined by mass spectrometry is : 637.21 (calculated value: 637.17); theoretical element content (%) C 36 H 21 F 6 N 5 : C, 67.82; H, 3.32; F, 17.88; N, 10.98, measured element content (%): C, 67.85; H, 3.30; F, 17.90; N, 10.92.
  • the above analysis results show that the obtained product is the target product.
  • Example 9 According to the synthesis of Example 9, the steps are the same, and the compound 2-chloro-4,6-bis(4-trifluoromethylphenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6- Diphenyl-1,3,5-triazine, 0.532g of white compound (yield 55.6%) was obtained.
  • the molecular ion mass determined by mass spectrometry analysis was 638.18 (calculated value: 638.17); theoretical element content (%) C 35 H 20 F 6 N 6 : C, 65.83; H, 3.16; F, 17.85; N, 13.16, measured element content (%): C, 65.85; H, 3.10; F, 17.86; N, 13.12.
  • the above analysis results show that the obtained product is the target product.
  • Example 49 According to the synthesis of Example 49, the steps were the same, and the compound 2-chloro-4,6-bis(4-trifluoromethylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6- Diphenyl-1,3,5-triazine, 0.511g of white compound (yield 46.6%) was obtained.
  • the molecular ion mass determined by mass spectrometry analysis was 829.24 (calculated value: 829.24); theoretical element content (%) C 49 H 29 F 6 N 7 : C, 70.92; H, 3.52; F, 13.74; N, 11.82, measured element content (%): C, 70.95; H, 3.54; F, 13.77; N, 11.90.
  • the above analysis results show that the obtained product is the target product.
  • Example 51 According to the synthesis of Example 51, the steps were the same, and the compound 2-chloro-4,6-bis(4-trifluoromethylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6- Diphenyl-1,3,5-triazine, 0.419g of white compound was obtained (yield 33.6%), the molecular ion mass determined by mass spectrometry analysis was: 831.24 (calculated value: 831.23); theoretical element content (%) C 47 H 27 F 6 N 9 : C, 67.87; H, 3.27; F, 13.70; N, 15.16, measured element content (%): C, 67.86; H, 3.29; F, 13.72; N, 15.14. The above analysis results show that the obtained product is the target product.
  • Example 53 According to the synthesis of Example 53, the steps were the same, and the compound 2-chloro-4,6-bis(4-trifluoromethylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6- Diphenyl-1,3,5-triazine, 0.446g of white compound was obtained (yield 35.8%), the molecular ion mass determined by mass spectrometry analysis was 831.20 (calculated value: 831.23); theoretical element content (%) C 47 H 27 F 6 N 9 : C, 67.87; H, 3.27; F, 13.70; N, 15.16, measured element content (%): C, 67.89; H, 3.33; F, 13.74; N, 15.18.
  • the above analysis results show that the obtained product is the target product.
  • Example 56 According to the synthesis of Example 56, the steps are the same, 2-chloro-4,6-bis(4-trifluoromethylphenyl)-1,3,5-triazine instead of the compound 2-chloro-4,6-diphenyl Yl-1,3,5-triazine, N-(3-trifluoromethylphenyl)-1,2-phenylenediamine instead of compound N-(3-fluorophenyl)-1,2-phenylenediamine , Obtain 0.583g of white compound (yield 40.3%), the molecular ion mass determined by mass spectrometry analysis is: 965.21 (calculated value: 965.21); theoretical element content (%) C 51 H 27 F 12 N 7 : C, 63.42; H, 2.82; F, 23.61; N, 10.15, measured element content (%): C, 63.45; H, 2.90; F, 23.63; N, 10.22. The above analysis results show that the obtained product is the target
  • Example 29 According to the synthesis of Example 29, the steps are the same, and the compound 2-chloro-4,6-bis(4-trifluoromethylphenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6- Diphenyl-1,3,5-triazine, N-(3,5-bis(trifluoromethyl)phenyl)-1,2-phenylenediamine instead of compound N-(3-fluorophenyl)- 1,2-Phenylenediamine, 0.594g of white compound (yield 51.2%) was obtained, the molecular ion mass determined by mass spectrometry analysis was: 773.18 (calculated value: 773.14); theoretical element content (%) C 38 H 19 F 12 N 5 : C, 59.00; H, 2.48; F, 29.47; N, 9.05, measured element content (%): C, 59.08; H, 2.53; F, 29.55; N, 9.12. The above analysis results show that the obtained product is
  • Example 49 According to the synthesis of Example 49, the steps are the same, using the compound N 1 , N 1 '- ⁇ 5-bromo-1,3-bis(2-trifluoromethylphenyl) ⁇ bis(1,2-phenylenediamine) Instead of compound N 1 , N 1 '(5-bromo-1,3-diphenyl)bis(1,2-phenylenediamine), 0.599g of white compound (yield 48.2%) was obtained, and the molecular ion was confirmed by mass spectrometry.
  • the above analysis results show that the obtained product is the target product.
  • Example 59 According to the synthesis of Example 59, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, the compound 3-trifluoromethylbenzaldehyde was substituted for the compound benzaldehyde to obtain 0.640g of a white compound (yield 44.2%).
  • the molecular ion mass determined by mass spectrometry was 965.23 (calculated value) Is: 965.21); theoretical element content (%) C 51 H 27 F 12 N 7 : C, 63.42; H, 2.82; F, 23.61; N, 10.15, measured element content (%): C, 63.48; H, 2.90 ; F, 23.66; N, 10.21.
  • the above analysis results show that the obtained product is the target product.
  • Example 19 According to the synthesis of Example 19, the steps were the same, and the compound N 1 -(2-isopropylphenyl)benzene-1,2-diamine was used instead of the compound N 1 -(2-fluorophenyl)benzene-1,2- Diamine, 0.523 g of white compound was obtained (yield 37.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.26 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 20 According to the synthesis of Example 20, the steps are the same, and the compound N 1 -(3-isopropylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(3-fluorophenyl)benzene-1,2- Diamine, 0.503 g of a white compound was obtained (yield 36.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.27 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 21 According to the synthesis of Example 21, the steps are the same, and the compound N 1 -(4-isopropylphenyl)benzene-1,2-diamine is substituted for the compound N 1 -(4-fluorophenyl)benzene-1,2- Diamine, 0.423 g of a white compound was obtained (yield 37.0%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.27 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 22 According to the synthesis of Example 22, the steps were the same, and the compound N 1 -(2-isopropylphenyl)benzene-1,2-diamine was used instead of the compound N 1 -(2-fluorophenyl)benzene-1,2- Diamine, 0.523 g of white compound was obtained (yield 37.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.26 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 23 According to the synthesis of Example 23, the steps were the same, and the compound N 1 -(3-isopropylphenyl)benzene-1,2-diamine was used instead of the compound N 1 -(3-fluorophenyl)benzene-1,2- Diamine, 0.578 g of a white compound was obtained (yield 33.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.27 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 24 According to the synthesis of Example 24, the steps were the same, and the compound N 1 -(4-isopropylphenyl)benzene-1,2-diamine was used instead of the compound N 1 -(4-fluorophenyl)benzene-1,2- Diamine, 0.513 g of a white compound was obtained (yield 36.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.29 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 25 According to the synthesis of Example 25, the steps are the same, and the compound N 1 -(2-isopropylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(2-fluorophenyl)benzene-1,2- Diamine, 0.523 g of white compound was obtained (yield 37.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.27 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 26 According to the synthesis of Example 26, the steps are the same, and the compound N 1 -(3-isopropylphenyl)benzene-1,2-diamine is substituted for the compound N 1 -(3-fluorophenyl)benzene-1,2- Diamine, 0.423 g of a white compound was obtained (yield 37.7%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.29 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 27 According to the synthesis of Example 27, the steps were the same, and the compound N 1 -(4-isopropylphenyl)benzene-1,2-diamine was used instead of the compound N 1 -(4-fluorophenyl)benzene-1,2- Diamine, 0.523 g of a white compound (yield 32.9%) was obtained.
  • the molecular ion mass determined by mass spectrometry analysis is: 543.28 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 28 According to the synthesis of Example 28, the steps are the same, and the compound N 1 -(3,5-diisopropylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(3,5-fluorophenyl)benzene -1,2-diamine, 0.523 g of a white compound was obtained (yield 37.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 585.26 (calculated value: 585.29); theoretical element content (%) C 40 H 35 N 5 : C, 82.02; H, 6.02; N, 11.96; measured element content (%): C, 82.05; H, 6.07; N, 11.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 29 According to the synthesis of Example 29, the steps are the same, and the compound N 1 -(3,5-diisopropylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(3,5-fluorophenyl)benzene -1,2-diamine, 0.520 g of white compound was obtained (yield 35.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 585.26 (calculated value: 585.29); theoretical element content (%) C 40 H 35 N 5 : C, 82.02; H, 6.02; N, 11.96; measured element content (%): C, 82.05; H, 6.07; N, 11.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 30 According to the synthesis of Example 30, the steps are the same, and the compound N 1 -(3,5-diisopropylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(3,5-fluorophenyl)benzene -1,2-diamine, 0.527 g of white compound was obtained (yield 35.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 585.27 (calculated value: 585.29); theoretical element content (%) C 40 H 35 N 5 : C, 82.02; H, 6.02; N, 11.96; measured element content (%): C, 82.05; H, 6.07; N, 11.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 31 According to the synthesis of Example 31, the procedure was the same, and the compound 2-isopropylbenzaldehyde was used instead of the compound 2-fluorobenzaldehyde to obtain 0.507 g of a white compound (yield 37.8%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.27 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 32 According to the synthesis of Example 32, the procedure was the same, and the compound 2-isopropylbenzaldehyde was substituted for the compound 2-fluorobenzaldehyde to obtain 0.523 g of a white compound (yield 37.6%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.27 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 33 According to the synthesis of Example 33, the procedure was the same, and the compound 2-isopropylbenzaldehyde was used instead of the compound 2-fluorobenzaldehyde to obtain 0.523 g of a white compound (yield 30.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.26 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 34 According to the synthesis of Example 34, the steps were the same, and the compound 3-isopropylbenzaldehyde was used instead of the compound 3-fluorobenzaldehyde to obtain 0.523 g of a white compound (yield 37.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.21 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 35 According to the synthesis of Example 35, the steps were the same, and the compound 3-isopropylbenzaldehyde was used instead of the compound 3-fluorobenzaldehyde to obtain 0.423 g of a white compound (yield 37.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.29 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 36 According to the synthesis of Example 36, the procedure was the same, and the compound 3-isopropylbenzaldehyde was substituted for the compound 3-fluorobenzaldehyde to obtain 0.479 g of a white compound (yield 37.1%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.23 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 37 According to the synthesis of Example 37, the procedure was the same, and the compound 4-isopropylbenzaldehyde was used instead of the compound 4-fluorobenzaldehyde to obtain 0.523 g of a white compound (yield 37.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.28 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 38 According to the synthesis of Example 38, the procedure was the same, and the compound 4-isopropylbenzaldehyde was used instead of the compound 4-fluorobenzaldehyde to obtain 0.523 g of a white compound (yield 37.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.22 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 39 According to the synthesis of Example 39, the procedure was the same, and the compound 4-isopropylbenzaldehyde was substituted for the compound 4-fluorobenzaldehyde to obtain 0.521 g of a white compound (yield 37.4%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.26 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 40 According to the synthesis of Example 40, the steps were the same, and the compound 3,5-diisopropylbenzaldehyde was substituted for the compound 3,5-difluorobenzaldehyde to obtain 0.514 g of a white compound (yield 31.4%).
  • the molecular ion mass determined by mass spectrometry analysis is: 585.26 (calculated value: 585.29); theoretical element content (%) C 40 H 35 N 5 : C, 82.02; H, 6.02; N, 11.96; measured element content (%): C, 82.05; H, 6.07; N, 11.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 41 According to the synthesis of Example 41, the steps are the same, and the compound 3,5-diisopropylbenzaldehyde is used instead of the compound 3,5-difluorobenzaldehyde to obtain 0.520 g of a white compound (yield 30.5%).
  • the molecular ion mass determined by mass spectrometry analysis is: 585.27 (calculated value: 585.29); theoretical element content (%) C 40 H 35 N 5 : C, 82.02; H, 6.02; N, 11.96; measured element content (%): C, 82.05; H, 6.07; N, 11.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 42 According to the synthesis of Example 42, the steps were the same, and the compound 3,5-diisopropylbenzaldehyde was used instead of the compound 3,5-difluorobenzaldehyde to obtain 0.523 g of a white compound (yield 37.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 585.27 (calculated value: 585.29); theoretical element content (%) C 40 H 35 N 5 : C, 82.02; H, 6.02; N, 11.96; measured element content (%): C, 82.05; H, 6.07; N, 11.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 55 According to the synthesis of Example 55, the steps were the same, and the compound N 1 -(2-isopropylphenyl)benzene-1,2-diamine was used instead of the compound N 1 -(2-fluorophenyl)benzene-1,2- Diamine, 0.529 g of a white compound was obtained (yield 27.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 777.30 (calculated value: 777.36); theoretical element content (%) C 53 H 43 N 7 : C, 81.83; H, 5.57; N, 12.60; measured element content (%): C, 81.85; H, 5.57; N, 12.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 56 According to the synthesis of Example 56, the steps are the same, and the compound N 1 -(3-isopropylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(3-fluorophenyl)benzene-1,2- Diamine, 0.579 g of a white compound (yield 24.2%) was obtained.
  • the molecular ion mass determined by mass spectrometry analysis is: 777.34 (calculated value: 777.36); theoretical element content (%) C 53 H 43 N 7 : C, 81.83; H, 5.57; N, 12.60; measured element content (%): C, 81.85; H, 5.57; N, 12.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 57 According to the synthesis of Example 57, the steps are the same, and the compound N 1 -(4-isopropylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(4-fluorophenyl)benzene-1,2- Diamine, 0.529 g of a white compound was obtained (yield 27.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 777.30 (calculated value: 777.36); theoretical element content (%) C 53 H 43 N 7 : C, 81.83; H, 5.57; N, 12.60; measured element content (%): C, 81.85; H, 5.57; N, 12.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 58 According to the synthesis of Example 58, the procedure was the same, and the compound 2-isopropylbenzaldehyde was used instead of the compound 2-fluorobenzaldehyde to obtain 0.529 g of a white compound (yield 27.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 777.32 (calculated value: 777.36); theoretical element content (%) C 53 H 43 N 7 : C, 81.83; H, 5.57; N, 12.60; measured element content (%): C, 81.85; H, 5.57; N, 12.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 59 According to the synthesis of Example 59, the steps were the same, and the compound 3-isopropylbenzaldehyde was used instead of the compound 3-fluorobenzaldehyde to obtain 0.529 g of a white compound (yield 27.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 777.30 (calculated value: 777.36); theoretical element content (%) C 53 H 43 N 7 : C, 81.83; H, 5.57; N, 12.60; measured element content (%): C, 81.85; H, 5.57; N, 12.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 60 According to the synthesis of Example 60, the steps were the same, and the compound 4-isopropylbenzaldehyde was used instead of the compound 4-fluorobenzaldehyde to obtain 0.629 g of a white compound (yield 29.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 777.32 (calculated value: 777.36); theoretical element content (%) C 53 H 43 N 7 : C, 81.83; H, 5.57; N, 12.60; measured element content (%): C, 81.85; H, 5.57; N, 12.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 61 According to the synthesis of Example 61, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, 0.529 g of a white compound (yield 27.2%) was obtained.
  • the molecular ion mass determined by mass spectrometry analysis is: 777.30 (calculated value: 777.36); theoretical element content (%) C 53 H 43 N 7 : C, 81.83; H, 5.57; N, 12.60; measured element content (%): C, 81.85; H, 5.57; N, 12.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 62 According to the synthesis of Example 62, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, 0.509 g of a white compound (yield 27.7%) was obtained.
  • the molecular ion mass determined by mass spectrometry analysis is: 777.32 (calculated value: 777.36); theoretical element content (%) C 53 H 43 N 7 : C, 81.83; H, 5.57; N, 12.60; measured element content (%): C, 81.85; H, 5.57; N, 12.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 63 According to the synthesis of Example 63, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, 0.529 g of a white compound (yield 27.2%) was obtained.
  • the molecular ion mass determined by mass spectrometry analysis is: 779.30 (calculated value: 779.35); theoretical element content (%) C 51 H 41 N 9 : C, 78.54; H, 5.30; N, 16.16; measured element content (%): C, 78.55; H, 5.37; N, 16.08.
  • the above analysis results show that the obtained product is the target product.
  • Example 64 According to the synthesis of Example 64, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, 0.428 g of a white compound (yield 25.6%) was obtained.
  • the molecular ion mass determined by mass spectrometry analysis is: 779.32 (calculated value: 779.35); theoretical element content (%) C 51 H 41 N 9 : C, 78.54; H, 5.30; N, 16.16; measured element content (%): C, 78.55; H, 5.37; N, 16.08.
  • the above analysis results show that the obtained product is the target product.
  • Example 65 According to the synthesis of Example 65, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, 0.529 g of a white compound (yield 27.2%) was obtained.
  • the molecular ion mass determined by mass spectrometry analysis is: 779.30 (calculated value: 779.35); theoretical element content (%) C 51 H 41 N 9 : C, 78.54; H, 5.30; N, 16.16; measured element content (%): C, 78.55; H, 5.37; N, 16.08.
  • the above analysis results show that the obtained product is the target product.
  • Example 66 According to the synthesis of Example 66, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, 0.427 g of a white compound (yield 25.7%) was obtained.
  • the molecular ion mass determined by mass spectrometry analysis is: 779.37 (calculated value: 779.35); theoretical element content (%) C 51 H 41 N 9 : C, 78.54; H, 5.30; N, 16.16; measured element content (%): C, 78.55; H, 5.37; N, 16.08.
  • the above analysis results show that the obtained product is the target product.
  • Example 67 According to the synthesis of Example 67, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, using compound N 1 -(2-isopropylphenyl)benzene-1,2-diamine instead of compound N 1 -(2-fluorophenyl) ) Benzene-1,2-diamine gave 0.529 g of white compound (yield 27.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 861.42 (calculated value: 861.45); theoretical element content (%): C 59 H 55 N 7 : C, 82.20; H, 6.43; N, 11.37; measured element content (%) : C, 82.25; H, 6.47; N, 11.28.
  • the above analysis results show that the obtained product is the target product.
  • Example 68 According to the synthesis of Example 68, the steps are the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, using compound N 1 -(3-isopropylphenyl)benzene-1,2-diamine instead of compound N 1 -(3-fluorophenyl) ) Benzene-1,2-diamine to obtain 0.565 g of a white compound (yield 28.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 861.41 (calculated value: 861.45); theoretical element content (%): C 59 H 55 N 7 : C, 82.20; H, 6.43; N, 11.37; measured element content (%) : C, 82.25; H, 6.48; N, 11.27.
  • the above analysis results show that the obtained product is the target product.
  • Example 69 According to the synthesis of Example 69, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, using compound N 1 -(4-isopropylphenyl)benzene-1,2-diamine instead of compound N 1 -(4-fluorophenyl) ) Benzene-1,2-diamine gave 0.529 g of white compound (yield 27.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 861.41 (calculated value: 861.45); theoretical element content (%): C 59 H 55 N 7 : C, 82.20; H, 6.43; N, 11.37; measured element content (%) : C, 82.25; H, 6.47; N, 11.28.
  • the above analysis results show that the obtained product is the target product.
  • Example 70 According to the synthesis of Example 70, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, using the compound 2-isopropyl-benzaldehyde instead of the compound 2-fluorobenzaldehyde to obtain 0.417 g of a white compound (yield 28.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 861.42 (calculated value: 861.45); theoretical element content (%): C 59 H 55 N 7 : C, 82.20; H, 6.43; N, 11.37; measured element content (%) : C, 82.25; H, 6.47; N, 11.28.
  • the above analysis results show that the obtained product is the target product.
  • Example 71 According to the synthesis of Example 71, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, using the compound 3-isopropylbenzaldehyde instead of the compound 3-fluoro-benzaldehyde to obtain 0.629 g of a white compound (yield 25.8%).
  • the molecular ion mass determined by mass spectrometry analysis is: 861.47 (calculated value: 861.45); theoretical element content (%): C 59 H 55 N 7 : C, 82.20; H, 6.43; N, 11.37; measured element content (%) : C, 82.25; H, 6.47; N, 11.28.
  • the above analysis results show that the obtained product is the target product.
  • Example 72 According to the synthesis of Example 72, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, using the compound 4-isopropylbenzaldehyde instead of the compound 4-fluorobenzaldehyde to obtain 0.529 g of a white compound (yield 27.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 861.42 (calculated value: 861.45); theoretical element content (%): C 59 H 55 N 7 : C, 82.20; H, 6.43; N, 11.37; measured element content (%) : C, 82.25; H, 6.47; N, 11.28.
  • the above analysis results show that the obtained product is the target product.
  • Example 73 According to the synthesis of Example 73, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, using compound N 1 -(3,5-diisopropylphenyl)benzene-1,2-diamine instead of compound N 1 -(3, 5-difluorophenyl)benzene-1,2-diamine gave 0.417 g of a white compound (yield 28.3%).
  • the molecular ion mass determined by mass spectrometry analysis is: 669.42 (calculated value: 669.38); theoretical element content (%): C 46 H 47 N 5 : C, 82.47; H, 7.07; N, 10.45; measured element content (%) : C, 82.45; H, 7.07; N, 10.48.
  • the above analysis results show that the obtained product is the target product.
  • Example 55 According to the synthesis of Example 55, the steps were the same, and the compound N 1 -(2-methylphenyl)benzene-1,2-diamine was used instead of the compound N 1 -(2-fluorophenyl)benzene-1,2-diamine. Amine, 0.509 g of a white compound was obtained (yield 27.7%).
  • the molecular ion mass determined by mass spectrometry analysis is: 721.32 (calculated value: 721.30); theoretical element content (%) C 49 H 35 N 7 : C, 81.53; H, 4.89; N, 13.58; measured element content (%): C, 81.55; H, 4.87; N, 13.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 56 According to the synthesis of Example 56, the steps are the same, and the compound N 1 -(3-methylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(3-fluorophenyl)benzene-1,2-diamine Amine, 0.644 g of a white compound was obtained (yield 25.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 721.31 (calculated value: 721.30); theoretical element content (%) C 49 H 35 N 7 : C, 81.53; H, 4.89; N, 13.58; measured element content (%): C, 81.55; H, 4.87; N, 13.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 57 According to the synthesis of Example 57, the steps are the same, and the compound N 1 -(4-methylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(4-fluorophenyl)benzene-1,2-diamine.
  • Amine, 0.519 g of a white compound was obtained (yield 27.7%).
  • the molecular ion mass determined by mass spectrometry analysis is: 721.32 (calculated value: 721.30); theoretical element content (%) C 49 H 35 N 7 : C, 81.53; H, 4.89; N, 13.58; measured element content (%): C, 81.55; H, 4.87; N, 13.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 58 According to the synthesis of Example 58, the procedure was the same, and the compound 2-methylbenzaldehyde was substituted for the compound 2-fluorobenzaldehyde to obtain 0.479 g of a white compound (yield 25.7%).
  • the molecular ion mass determined by mass spectrometry analysis is: 721.37 (calculated value: 721.30); theoretical element content (%) C 49 H 35 N 7 : C, 81.53; H, 4.89; N, 13.58; measured element content (%): C, 81.55; H, 4.87; N, 13.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 59 According to the synthesis of Example 59, the procedure was the same, and the compound 3-methylbenzaldehyde was used instead of the compound 3-fluorobenzaldehyde to obtain 0.509 g of a white compound (yield 27.5%).
  • the molecular ion mass determined by mass spectrometry analysis is: 721.32 (calculated value: 721.30); theoretical element content (%) C 49 H 35 N 7 : C, 81.53; H, 4.89; N, 13.58; measured element content (%): C, 81.55; H, 4.87; N, 13.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 60 According to the synthesis of Example 60, the steps were the same, and the compound 4-methylbenzaldehyde was substituted for the compound 4-fluorobenzaldehyde to obtain 0.578 g of a white compound (yield 23.8%).
  • the molecular ion mass determined by mass spectrometry analysis is: 721.32 (calculated value: 721.30); theoretical element content (%) C 49 H 35 N 7 : C, 81.53; H, 4.89; N, 13.58; measured element content (%): C, 81.55; H, 4.87; N, 13.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 61 According to the synthesis of Example 61, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine gave 0.529 g of a white compound (yield 27.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 721.32 (calculated value: 721.30); theoretical element content (%) C 49 H 35 N 7 : C, 81.53; H, 4.89; N, 13.58; measured element content (%): C, 81.55; H, 4.87; N, 13.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 62 According to the synthesis of Example 62, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine gave 0.479 g of a white compound (yield 25.4%).
  • the molecular ion mass determined by mass spectrometry analysis is: 721.30 (calculated value: 721.30); theoretical element content (%) C 49 H 35 N 7 : C, 81.53; H, 4.89; N, 13.58; measured element content (%): C, 81.55; H, 4.87; N, 13.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 63 According to the synthesis of Example 63, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, 0.529 g of a white compound was obtained (yield 27.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 723.30 (calculated value: 723.29); theoretical element content (%) C 47 H 33 N 9 : C, 77.99; H, 4.60; N, 17.42; measured element content (%): C, 77.95; H, 4.67; N, 17.38.
  • the above analysis results show that the obtained product is the target product.
  • Example 64 According to the synthesis of Example 64, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, 0.439 g of a white compound was obtained (yield 26.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 723.31 (calculated value: 723.29); theoretical element content (%) C 47 H 33 N 9 : C, 77.99; H, 4.60; N, 17.42; measured element content (%): C, 77.95; H, 4.67; N, 17.38.
  • the above analysis results show that the obtained product is the target product.
  • Example 65 According to the synthesis of Example 65, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine to obtain 0.529 g of a white compound (yield 27.1%).
  • the molecular ion mass determined by mass spectrometry analysis is: 723.30 (calculated value: 723.29); theoretical element content (%) C 47 H 33 N 9 : C, 77.99; H, 4.60; N, 17.42; measured element content (%): C, 77.95; H, 4.67; N, 17.38.
  • the above analysis results show that the obtained product is the target product.
  • Example 66 According to the synthesis of Example 66, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, 0.671 g of a white compound was obtained (yield 28.3%).
  • the molecular ion mass determined by mass spectrometry analysis is: 723.30 (calculated value: 723.29); theoretical element content (%) C 47 H 33 N 9 : C, 77.99; H, 4.60; N, 17.42; measured element content (%): C, 77.95; H, 4.67; N, 17.38.
  • the above analysis results show that the obtained product is the target product.
  • Example 67 According to the synthesis of Example 67, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, using compound N 1 -(2-methylphenyl)benzene-1,2-diamine instead of compound N 1 -(2-fluorophenyl)benzene -1,2-Diamine to obtain 0.529 g of a white compound (yield 27.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 749.36 (calculated value: 749.33); theoretical element content (%) C 51 H 39 N 7 : C, 81.68; H, 5.24; N, 13.07; measured element content (%): C, 81.65; H, 5.27; N, 13.08.
  • the above analysis results show that the obtained product is the target product.
  • Example 68 According to the synthesis of Example 68, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, using compound N 1 -(3-methylphenyl)benzene-1,2-diamine instead of compound N 1 -(3-fluorophenyl)benzene -1,2-Diamine to obtain 0.679 g of a white compound (yield 29.7%).
  • the molecular ion mass determined by mass spectrometry analysis is: 749.32 (calculated value: 749.33); theoretical element content (%) C 51 H 39 N 7 : C, 81.68; H, 5.24; N, 13.07; measured element content (%): C, 81.65; H, 5.27; N, 13.08.
  • the above analysis results show that the obtained product is the target product.
  • Example 69 According to the synthesis of Example 69, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, using compound N 1 -(4-methylphenyl)benzene-1,2-diamine instead of compound N 1 -(4-fluorophenyl)benzene -1,2-Diamine to obtain 0.508 g of a white compound (yield 24.7%).
  • the molecular ion mass determined by mass spectrometry analysis is: 749.31 (calculated value: 749.33); theoretical element content (%) C 51 H 39 N 7 : C, 81.68; H, 5.24; N, 13.07; measured element content (%): C, 81.65; H, 5.27; N, 13.08.
  • the above analysis results show that the obtained product is the target product.
  • Example 70 According to the synthesis of Example 70, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, using the compound 2-methylbenzaldehyde instead of the compound 2-fluorobenzaldehyde to obtain 0.679 g of a white compound (yield 29.7%).
  • the molecular ion mass determined by mass spectrometry analysis is: 749.31 (calculated value: 749.33); theoretical element content (%) C 51 H 39 N 7 : C, 81.68; H, 5.24; N, 13.07; measured element content (%): C, 81.65; H, 5.27; N, 13.08.
  • the above analysis results show that the obtained product is the target product.
  • Example 71 According to the synthesis of Example 71, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, the compound 3-methylbenzaldehyde was substituted for the compound 3-fluorobenzaldehyde to obtain 0.577 g of a white compound (yield 26.5%).
  • the molecular ion mass determined by mass spectrometry analysis is: 749.37 (calculated value: 749.33); theoretical element content (%) C 51 H 39 N 7 : C, 81.68; H, 5.24; N, 13.07; measured element content (%): C, 81.65; H, 5.27; N, 13.08.
  • the above analysis results show that the obtained product is the target product.
  • Example 72 According to the synthesis of Example 72, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, using the compound 4-methylbenzaldehyde instead of the compound 4-fluorobenzaldehyde to obtain 0.792 g of a white compound (yield 23.7%).
  • the molecular ion mass determined by mass spectrometry analysis is: 749.31 (calculated value: 749.33); theoretical element content (%) C 51 H 39 N 7 : C, 81.68; H, 5.24; N, 13.07; measured element content (%): C, 81.65; H, 5.27; N, 13.08.
  • the above analysis results show that the obtained product is the target product.
  • Example 73 According to the synthesis of Example 73, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, using compound N 1 -(3,5-dimethylphenyl)benzene-1,2-diamine instead of compound N 1 -(3,5- Difluorophenyl)benzene-1,2-diamine gave 0.679 g of a white compound (yield 29.7%).
  • the molecular ion mass determined by mass spectrometry analysis is: 557.29 (calculated value: 557.26); theoretical element content (%) C 38 H 31 N 5 : C, 81.84; H, 5.60; N, 12.56; measured element content (%): C, 81.85; H, 5.67; N, 12.48.
  • the above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps are the same, the compound N 1 -([1,1'-biphenyl]-2-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.435g of a white compound (Yield 31.3%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.25 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 2 According to the synthesis of Example 2, the steps are the same, and the compound N 1 -([1,1'-biphenyl]-2-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.467g of a white compound (Yield 31.6%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.28 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 3 According to the synthesis of Example 3, the steps are the same, the compound N 1 -([1,1'-biphenyl]-2-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.438 g of a white compound (Yield 32.7%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.29 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 4 According to the synthesis of Example 4, the steps were the same, and the compound [1,1'-biphenyl]-2-carbaldehyde was used instead of the compound benzaldehyde to obtain 0.503 g of a white compound (yield 35.4%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.32 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 5 According to the synthesis of Example 5, the steps were the same, and the compound [1,1'-biphenyl]-2-carbaldehyde was used instead of the compound benzaldehyde to obtain 0.468 g of a white compound (yield 30.3%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.31 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 6 According to the synthesis of Example 6, the steps were the same, and the compound [1,1'-biphenyl]-2-carbaldehyde was used instead of the compound benzaldehyde to obtain 0.538 g of a white compound (yield 38.3%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.30 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps are the same, the compound N 1 -([1,1'-biphenyl]-3-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.492g of a white compound (Yield 34.6%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.28 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 2 According to the synthesis of Example 2, the steps are the same, the compound N 1 -([1,1'-biphenyl]-3-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.448g of a white compound (Yield 32.8%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.28 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 3 According to the synthesis of Example 3, the steps are the same, the compound N 1 -([1,1'-biphenyl]-3-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.523g of a white compound (Yield 31.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.21 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 4 According to the synthesis of Example 4, the steps were the same, and the compound [1,1'-biphenyl]-3-carbaldehyde was substituted for the compound benzaldehyde to obtain 0.495 g of a white compound (yield 33.1%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.20 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 5 According to the synthesis of Example 5, the steps were the same, and the compound [1,1'-biphenyl]-3-carbaldehyde was used instead of the compound benzaldehyde to obtain 0.441 g of a white compound (yield 32.1%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.28 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 6 According to the synthesis of Example 6, the steps are the same, using [1,1'-biphenyl]-3-carbaldehyde instead of the compound benzaldehyde to obtain 0.438 g of a white compound (yield 32.4%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.25 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps are the same, and the compound N 1 -([1,1'-biphenyl]-4-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.413g of a white compound (Yield 35.6%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.30 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 2 According to the synthesis of Example 2, the steps are the same, and the compound N 1 -([1,1'-biphenyl]-4-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.448g of a white compound (Yield 31.3%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.26 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 3 According to the synthesis of Example 3, the steps are the same, and the compound N 1 -([1,1'-biphenyl]-4-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.458g of a white compound (Yield 33.8%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.28 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 4 According to the synthesis of Example 4, the steps were the same, and the compound [1,1'-biphenyl]-4-carbaldehyde was used instead of the compound benzaldehyde to obtain 0.531 g of a white compound (yield 36.7%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.29 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 5 According to the synthesis of Example 5, the steps were the same, and [1,1'-biphenyl]-4-carbaldehyde was used instead of the compound benzaldehyde to obtain 0.538 g of a white compound (yield 34.3%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.31 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 6 According to the synthesis of Example 6, the steps are the same, using [1,1'-biphenyl]-4-carbaldehyde instead of the compound benzaldehyde to obtain 0.527 g of a white compound (yield 36.7%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.25 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • the specific device preparation process is as follows: transparent ITO glass is used as the base material for the preparation of the device, and then ultrasonically treated with 5% ITO lotion for 30 minutes, followed by distilled water (2 times ), acetone (2 times), isopropanol (2 times) ultrasonic washing, and finally the ITO glass is stored in isopropanol. Before each use, carefully wipe the surface of the ITO glass with an acetone cotton ball and an isopropyl alcohol cotton ball, rinse it with isopropyl alcohol and dry it, and then treat it with plasma for 5 minutes. The device is prepared by vacuum coating equipment using vacuum evaporation process.
  • the deposition rate is determined by Sainz Film Thickness Meter using vacuum evaporation process.
  • Various organic layers, LiF electron injection layers and metal Al electrodes are sequentially deposited on the ITO glass (see the following effect examples for specific device structures).
  • the current, voltage, brightness, luminescence spectrum and other characteristics of the device are tested simultaneously with PR 650 spectral scanning luminance meter and Keithley K 2400 digital source meter system.
  • the performance test of the device is carried out in anhydrous and oxygen-free glove box.
  • HATCN is used as the hole injection layer
  • DBBA is used as the first hole transport layer
  • TCTA is used as the second hole
  • the transport layer is used.
  • TCTA is mixed with the compound 1-171 of the present invention as a host material (the weight mixing ratio of TCTA and compound 1-171 is 1:1), and the compound 1-171 of the present invention is used as a host material. Used as an electronic transmission material.
  • the structure of the organic electroluminescent device is [ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA:n+10wt%IrPPy 3 /n(30nm)/LiF(1nm)/Al(100nm) )].
  • n represents the compound number: 1-171.
  • the compound used in the host material is the same as that used in the electron transport layer, and IrPPy 3 is used as the doped luminescent material (the weight ratio doping concentration is 10WT%).
  • Table 1-1 The results of the effect examples are shown in Table 1-1.
  • HATCN was used as the hole injection layer
  • DBBA was used as the first hole transport layer
  • TCTA was used as the second hole transport layer Use
  • TCTA is mixed with 3P-T2T, E1 or E2 as the host material.
  • the two materials are mixed in a weight ratio of 1:1, and IrPPy 3 doped luminescent material is used (the weight ratio doping concentration is 10WT%), 3P-T2T, E1 or E2 are used as electron transport materials at the same time.
  • Comparative Examples 1-1 to 3-1 organic electroluminescent device structure is [ITO/HATCN (5nm)/DBBA (60nm)/TCTA (10nm)/TCTA: 3P-T2T or E1 or E2+10wt% IrPPy 3 / 3P-T2T or E1 or E2(30nm)/LiF(1nm)/Al(100nm)].
  • HATCN was used as the hole injection layer
  • DBBA was used as the first hole transport layer
  • TCTA was used as the second hole transport layer
  • TBT-07, TBT-14, ET85, 1, 3, 4, 130, 135, 150, 160, 165, and 170 are used as electron transport layer (ETL) materials, respectively. Used as a host material in the light-emitting layer.
  • ETL electron transport layer
  • Comparative Examples 4-1 to 15-1 organic electroluminescent device structure is [ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/n+10wt%IrPPy 3 /n(30nm)/LiF(1nm) )/Al(100nm)].
  • n represents the compound number.
  • the compound used in the host material is the same as that used in the electron transport layer, and IrPPy 3 is used as the doped luminescent material (the weight ratio doping concentration is 10WT%).
  • Table 2-1 The results of the comparative example are shown in Table 2-1.
  • Test data of the device of the embodiment under the condition of a drive current density of 10 mA/cm 2 (constant current drive mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
  • Test data of the comparative example device under the condition of a drive current density of 10 mA/cm 2 (constant current drive mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
  • the 1,3,5-triazine compound of the present invention is used as the electron transport layer, and at the same time as the electron acceptor material and the electron donor material to construct the light emitting layer.
  • luminance organic electroluminescent device up to 8310cd / m 2 -8960cd / m 2 ; the current efficiency of up to 79cd / a-91cd / a; device life up to 1023 hours -1299 hours (T90).
  • the brightness of the organic electroluminescent device prepared by using the above compound as the electron transport layer and at the same time as the electron acceptor material to construct the light emitting layer is 5082cd/m 2 -5810cd/m 2 ; Current efficiency is 52cd/A-57cd/A; device lifetime is 410 hours-690 hours (T90).
  • HATCN is used as the hole injection layer
  • DBBA is used as the first hole transport layer
  • TCTA is used as the second hole
  • the transport layer is used.
  • TCTA is mixed with the compound 1-171 of the present invention as a host material (the weight mixing ratio of TCTA and compound 1-171 is 1:1), and TPBI is used as an electron transport material.
  • the structure of the organic electroluminescent device is [ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA:n+10wt%IrPPy 3 /TPBI(30nm)/LiF(1nm)/Al(100nm) )].
  • n represents the compound number: 1-171.
  • the compound used in the host material is the same as that used in the electron transport layer, and IrPPy 3 is used as the doped luminescent material (the weight ratio doping concentration is 10WT%).
  • Table 1-2 The results of the effect examples are shown in Table 1-2.
  • HATCN was used as the hole injection layer
  • DBBA was used as the first hole transport layer
  • TCTA was used as the second hole transport layer Use
  • TCTA is mixed with one of 3P-T2T, E1, E2, TBT-07, TBT-14 and ET85 as the host material in the light-emitting layer, the two materials are mixed in a weight ratio of 1:1, and IrPPy 3 doped light-emitting material. (Weight ratio doping concentration is 10WT%)
  • TPBI is used as an electron transport material.
  • Organic electroluminescent device structure is [ITO/HATCN (5nm)/DBBA (60nm)/TCTA (10nm)/TCTA: 3P-T2T, E1, E2, TBT-07, TBT -14 or ET85+10wt% IrPPy 3 /TPBI(30nm)/LiF(1nm)/Al(100nm)].
  • HATCN was used as the hole injection layer
  • DBBA was used as the first hole transport layer
  • TCTA was used as the second hole transport layer
  • Compounds 1, 3 , 4 , 130, 135, 150, 160, 165 and 170 in the layer are used as host materials
  • IrPPy 3 is used as doped luminescent material (weight ratio doping concentration is 10WT%)
  • TPBI is used as electron Use of transmission materials.
  • Comparative Examples 7-2 to 15-2 organic electroluminescent device structures are [ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/n+10wt%IrPPy 3 /TPBI(30nm)/LiF(1nm) )/Al(100nm)].
  • the results of the comparative example are shown in Table 2-2.
  • Test data of the device of the embodiment under the condition of a driving current density of 10 mA/cm 2 (constant current driving mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
  • Test data of the comparative example device under the condition of a drive current density of 10 mA/cm 2 (constant current drive mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
  • the 1,3,5-triazine compound of the present invention is used as the electron acceptor material and the electron donor material to construct the light emitting layer, and the prepared organic electroluminescent device is Brightness can reach 7087cd/m 2 -7981cd cd/m 2 ; current efficiency can reach 72cd/A-83cd/A; device life can reach 827 hours -985 hours (T90).
  • the organic electroluminescent device prepared by using the 1,3,5-triazine compound of the present invention as the electron acceptor material and the electron donor material to construct the light emitting layer is prepared by the light emitting layer constructed with the above compound Compared with the organic electroluminescent device, the brightness is increased by 22.6%-57%, the current efficiency is increased by 14%-73%, and the life of the device is increased by 23%-140%.
  • HATCN is used as the hole injection layer
  • DBBA is used as the first hole transport layer
  • TCTA is used as the second hole
  • the transport layer is used
  • TCTA is used as the host material in the light-emitting layer
  • compound 1-171 is used as the electron transport material.
  • Effect Example The structure of the organic electroluminescent device is [ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA+10wt%IrPPy 3 /n(30nm)/LiF(1nm)/Al(100nm)] .
  • n represents the compound number: 1-171.
  • the compound used in the host material is the same as that used in the electron transport layer, and IrPPy 3 is used as the doped luminescent material (the weight ratio doping concentration is 10WT%).
  • the results of the effect examples are shown in Table 1-3.
  • HATCN was used as the hole injection layer
  • DBBA was used as the first hole transport layer
  • TCTA was used as the second hole transport layer Use
  • TCTA as the host material in the light-emitting layer
  • IrPPy 3 doped light-emitting material weight ratio doping concentration of 10WT%
  • 3P-T2T, E1, E2, TBT-07, TBT-14 and ET85 are used as Use of electronic transmission materials.
  • Comparative Examples 1-3 to 6-3 organic electroluminescent device structure is [ITO/HATCN (5nm)/DBBA (60nm)/TCTA (10nm)/TCTA+10wt% IrPPy 3 /3P-T2T, E1, E2, TBT-07, TBT-14 or ET85(30nm)/LiF(1nm)/Al(100nm)].
  • the results of the comparative example are shown in Table 2-3.
  • Test data of the device of the embodiment under the condition of a driving current density of 10 mA/cm 2 (constant current driving mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
  • Test data of the comparative example device under the condition of a driving current density of 10 mA/cm 2 (constant current driving mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
  • the brightness of the organic electroluminescent device prepared by using the 1,3,5-triazine compound of the present invention as the electron transport layer can reach 6371cd/m 2 -7069cd/ m 2 ; current efficiency can reach 65cd/A-75cd/A; device lifetime can reach 746 hours-877 hours (T90).
  • the organic electroluminescent device prepared by using the compound in the above comparative example as the electron transport layer has a brightness of 4862cd/m 2 -5196cd/m 2 and a current efficiency of 50cd/ A-56cd/A; device life is 361 hours -496 hours (T90).
  • the 1,3,5-triazine compound of the present invention is compared with the above-mentioned existing compounds, and the brightness of the organic electroluminescent device prepared as the electron transport layer is increased by 22.6%-45.4%, and the current efficiency Increased by 16%-50%; device life increased by 50%-143%.
  • HATCN is used as the hole injection layer
  • DBBA is used as the first hole transport layer
  • TCTA is used as the second hole
  • the transport layer is used.
  • TCTA is mixed with the compound 1-171 of the present invention as a host material (the weight mixing ratio of TCTA and compound 1-171 is 1:1), and the compound 1-179 of the present invention is used as a host material. Used as an electronic transmission material.
  • the structure of the organic electroluminescent device is [ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA:n+1wt%DPh2AAN/n(30nm)/LiF(1nm)/Al(100nm) ].
  • n represents the compound number: 1-171.
  • the compound used in the host material is the same as the compound used in the electron transport layer, and DPh2AAN is used as the doped luminescent material (weight ratio doping concentration is 1WT%).
  • the results of the effect examples are shown in Table 1-5.
  • HATCN was used as the hole injection layer
  • DBBA was used as the first hole transport layer
  • TCTA was used as the second hole transport layer Use
  • TCTA is mixed with 3P-T2T, E1 or E2 as the host material in the light-emitting layer, the two materials are mixed in a weight ratio of 1:1
  • DPh2AAN doped luminescent material is used (weight ratio doping concentration is 1WT%)
  • 3P -T2T, E1 or E2 are used as electron transport materials respectively.
  • Comparative Examples 1-1 to 3-1 organic electroluminescent device structure is [ITO/HATCN (5nm)/DBBA (60nm)/TCTA (10nm)/TCTA: 3P-T2T or E1 or E2+10wt%DPh2AAN/3P -T2T or E1 or E2(30nm)/LiF(1nm)/Al(100nm)].
  • Test data of the device of the embodiment under the condition of a driving current density of 10 mA/cm 2 (constant current driving mode) (device life T90 represents the time it takes for the brightness of the device to decay to 90% of the initial brightness).
  • Test data of the comparative example device under the condition of a driving current density of 10 mA/cm 2 (constant current driving mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
  • the 1,3,5-triazine compound of the present invention is used as the electron transport layer, and at the same time as the electron acceptor material and the electron donor material to construct the light emitting layer, the prepared
  • the brightness of the electroluminescent device can reach 3501cd/m 2 -3900cd/m 2 ; the current efficiency can reach 54cd/A-62cd/A; the lifetime of the device can reach 910 hours -990 hours (T90).
  • the brightness of the organic electroluminescent device prepared by using the above compound as the electron transport layer and at the same time as the electron acceptor material to construct the light-emitting layer is 2350cd/m 2 -2571cd/m 2 ;
  • the current efficiency is 39cd/A-41cd/A;
  • the device life is 402 hours-462 hours (T90).
  • HATCN is used as the hole injection layer
  • DBBA is used as the first hole transport layer
  • TCTA is used as the second hole
  • the transport layer is used.
  • TCTA is mixed with the compound 1-171 of the present invention as a host material (the weight mixing ratio of TCTA and compound 1-179 is 1:1), and TPBI is used as an electron transport material.
  • the structure of the organic electroluminescent device is [ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA:n+1wt%DPh2AAN/TPBI(30nm)/LiF(1nm)/Al(100nm) ].
  • n represents the compound number: 1-179
  • DPh2AAN is used as a doped luminescent material (weight ratio doping concentration is 1WT%).
  • Table 1-5 The results of the effect examples are shown in Table 1-5.
  • HATCN was used as the hole injection layer
  • DBBA was used as the first hole transport layer
  • TCTA was used as the second hole transport layer Use
  • TCTA is mixed with 3P-T2T, E1 or E2 as the host material in the light-emitting layer, the two materials are mixed in a weight ratio of 1:1
  • DPh2AAN doped luminescent material is used (weight ratio doping concentration is 1WT%)
  • TPBI Used as an electronic transmission material.
  • Comparative Examples 1-5 to 3-5 organic electroluminescent device structure is [ITO/HATCN (5nm)/DBBA (60nm)/TCTA (10nm)/TCTA: 3P-T2T or E1 or E2+10wt%DPh2AAN/TPBI (30nm)/LiF(1nm)/Al(100nm)].
  • Test data of the device of the embodiment under the condition of a driving current density of 10 mA/cm 2 (constant current driving mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
  • Test data of the comparative example device under the condition of a driving current density of 10 mA/cm 2 (constant current driving mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
  • the 1,3,5-triazine compound of the present invention is used as the electron acceptor material and the electron donor material to construct the light emitting layer, and the brightness of the organic electroluminescent device prepared is It can reach 3205cd/m 2 -3600cd/m 2 ; current efficiency can reach 47cd/A-56cd/A; device life can reach 650 hours -750 hours (T90).
  • the organic electroluminescent device prepared by using the above compound as the electron acceptor material to construct the luminescent layer has a brightness of 2032cd/m 2 -2205cd/m 2 and a current efficiency of 34cd/A -38cd/A; device lifetime is 342 hours -375 hours (T90).
  • the 1,3,5-triazine compound of the present invention is used as an electron acceptor material to construct a light-emitting layer, and the brightness of the organic electroluminescent device prepared by using the 1,3,5-triazine compound of the present invention is increased by 45%-77. %, the current efficiency is increased by 23.7% to 64.7%; the device life is increased by 73% to 119%.
  • the mother nucleus of the 1,3,5-triazine compound shown in formula I of the present invention is a benzene ring linked by a single bond
  • the molecular structure of a triazine and one or more benzimidazoles is relatively complicated, and it is mainly manifested in: (1) A triazine heterocycle and one or more benzimidazole heterocycles constitute a complex compound heterocyclic system; (2) A triazine derivative and one or more benzenes are linked by a single bond on the periphery of a benzene ring
  • the molecular conformational structure of this molecule is very complicated; (3) Triazine derivatives and benzimidazole derivatives are both electron-deficient groups, and triazine derivatives are stronger than benzimidazole derivatives Due to the lack of electrons, this molecule will have certain intramolecular charge transfer characteristics.
  • the molecular weight of the target molecule can be adjusted in a larger range by introducing different substituent groups, and thus the molecular weight of the target molecule can be adjusted in a wider range.
  • the sublimation temperature of the target molecule is adjusted within the range (200-450°C), which is advantageous for selecting matching materials that are close to the sublimation temperature of the target product.
  • a good electron transport material may not necessarily be a good host material.
  • As a good host material it should generally have balanced and good electron and hole transport properties.
  • the properties of the host material also depend on the carrier transport properties of the matched doped luminescent material and the overall carrier transport properties of the doped film after doping. For example, if a host material dominated by electron transport is matched with a doped material with a certain hole transport ability, it is possible to obtain better results, and if it is matched with a doped material with a certain electron transport ability, it is possible to obtain a poor effect. .
  • the carrier transport performance of the composite film obtained after the host/guest doping is often not a simple superposition of the two separate properties.
  • the carrier transport performance of the doped composite film is difficult to accurately predict, and specific experiments must be conducted.
  • the analysis and verification party can obtain the ideal matching combination.
  • the host material composed of the two-component electron donor and electron acceptor will be more complicated, and its performance is also difficult to accurately infer based on experience.
  • the existing compounds E1, E2 or 3P-T2T are used as one of the electron transport material and the host material of the light-emitting layer at the same time, or only as one of the host materials of the light-emitting layer.
  • the efficiency and lifetime of the prepared organic electroluminescent device are not significantly improved.
  • CN102593374B discloses the compound TPT-07 as an electron transport layer, or as an electron transport layer, it is used as a host material for the preparation of electroluminescent devices. However, the efficiency of the prepared light-emitting device is still low.
  • the compound of the present invention when used as a combination of electron acceptor material and electron donor material, when used as the host material of the light-emitting layer, under the same driving current density,
  • the brightness, efficiency and lifetime of the prepared organic electroluminescent device are significantly higher than that of the materials disclosed in the prior art; further, when the compound of the present invention is used as an electron transport layer, it is used as an electron acceptor material and an electron donor material at the same time
  • the light-emitting layer is constructed, and the organic electroluminescent device prepared under the same driving current density can obtain better brightness, efficiency and lifetime.
  • the stability of the device has the most obvious technical effect advantage.

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne un composé de 1,3,5-triazine substitué, une composition et une utilisation associées. La présente invention concerne un composé de 1,3,5-triazine représenté par la formule I. Le composé de 1,3,5-triazine selon la présente invention peut être utilisé non seulement dans un matériau de transport d'électrons, mais également dans un matériau accepteur d'électrons. Le composé peut être utilisé pour préparer une couche de transport d'électrons ou est utilisé en combinaison avec une composition d'un matériau donneur d'électrons pour servir de matériau de base d'un dispositif électroluminescent, de sorte que le dispositif électroluminescent obtenu par la préparation présente des avantages tels qu'une efficacité élevée et une longue durée de vie. Le composé de 1,3,5-triazine fourni par la présente invention utilisé en tant que couche de transport d'électrons, peut être également utilisé en combinaison avec une composition d'un matériau donneur d'électrons en tant que matériau accepteur d'électrons pour fabriquer une couche électroluminescente, de sorte que le dispositif électroluminescent obtenu peut avoir des caractéristiques avantageuses telles qu'une meilleure efficacité et une durée de vie plus longue.
PCT/CN2020/081035 2019-03-29 2020-03-25 Composé de 1,3,5-triazine substitué, composition et utilisation associées WO2020199996A1 (fr)

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